From 754432f029002dac24c5ec2ca73ac320dd450440 Mon Sep 17 00:00:00 2001
From: Brian Krabach <brkrabac@microsoft.com>
Date: Tue, 28 Jan 2025 14:55:31 -0800
Subject: [PATCH] adds support for o1 (non-preview) model for openai_client,
 improves handling of context for codespace-assistant (#308)

NOTE: suggested that you re-run root level `make` if merging this update
into your environment where you already have your packages installed, in
order to cause the updated `openai` and `tiktoken` packages to be
loaded.
---
 .../codespace-assistant/assistant/config.py   |    2 +-
 .../extensions/tools/__mcp_server_configs.py  |   28 +-
 .../assistant/response/completion_handler.py  |    6 +-
 .../assistant/response/response.py            |    8 +-
 .../assistant/response/step_handler.py        |   33 +-
 .../assistant/response/utils/openai_utils.py  |    1 +
 assistants/codespace-assistant/pyproject.toml |    3 +-
 assistants/codespace-assistant/uv.lock        |   54 +-
 .../explorer-assistant/.vscode/launch.json    |    1 +
 .../assistant/response/response_openai.py     |   35 +-
 assistants/explorer-assistant/pyproject.toml  |    2 +-
 assistants/explorer-assistant/uv.lock         | 1318 ++++----
 .../pyproject.toml                            |    8 +-
 .../guided-conversation-assistant/uv.lock     |   62 +-
 .../prospector-assistant/pyproject.toml       |    2 +-
 assistants/prospector-assistant/uv.lock       |   62 +-
 assistants/skill-assistant/pyproject.toml     |    2 +-
 assistants/skill-assistant/uv.lock            |   26 +-
 .../python/python-01-echo-bot/pyproject.toml  |    2 +-
 examples/python/python-01-echo-bot/uv.lock    |   12 +-
 .../python-02-simple-chatbot/pyproject.toml   |    8 +-
 .../python/python-02-simple-chatbot/uv.lock   |   62 +-
 .../pyproject.toml                            |    8 +-
 .../python-03-multimodel-chatbot/uv.lock      |   62 +-
 libraries/python/anthropic-client/uv.lock     |   20 +-
 .../assistant_extensions/ai_clients/model.py  |    2 +-
 .../assistant-extensions/pyproject.toml       |    2 +-
 libraries/python/assistant-extensions/uv.lock |   18 +-
 .../python/content-safety/pyproject.toml      |    6 +-
 libraries/python/content-safety/uv.lock       |   14 +-
 .../openai-client/openai_client/client.py     |    2 +-
 .../openai-client/openai_client/config.py     |   16 +-
 .../openai-client/openai_client/messages.py   |   20 +-
 .../openai-client/openai_client/tokens.py     |   20 +-
 libraries/python/openai-client/pyproject.toml |    4 +-
 libraries/python/openai-client/uv.lock        | 1432 ++++----
 libraries/python/skills/notebooks/uv.lock     |   60 +-
 .../skills/skill-library/pyproject.toml       |    2 +-
 libraries/python/skills/skill-library/uv.lock |   20 +-
 .../python/skills/skills/common-skill/uv.lock |   60 +-
 .../skills/skills/document-skill/uv.lock      |   58 +-
 .../skills/skills/form-filler-skill/uv.lock   |   22 +-
 .../skills/guided-conversation-skill/uv.lock  |   60 +-
 .../python/skills/skills/posix-skill/uv.lock  |   58 +-
 .../skills/skills/prospector-skill/uv.lock    |   58 +-
 .../skills/skills/skill-template/uv.lock      |   58 +-
 workspaces-app/.vscode/settings.json          |    3 +
 workspaces-app/README.md                      |   78 +-
 workspaces-app/package.json                   |   18 +-
 workspaces-app/pnpm-lock.yaml                 | 2870 +++++++++++++++++
 workspaces-app/src/App.tsx                    |   14 +
 workspaces-app/src/index.tsx                  |   21 +
 52 files changed, 5046 insertions(+), 1777 deletions(-)
 create mode 100644 workspaces-app/.vscode/settings.json
 create mode 100644 workspaces-app/pnpm-lock.yaml
 create mode 100644 workspaces-app/src/App.tsx
 create mode 100644 workspaces-app/src/index.tsx

diff --git a/assistants/codespace-assistant/assistant/config.py b/assistants/codespace-assistant/assistant/config.py
index 226121fb..cd9daec1 100644
--- a/assistants/codespace-assistant/assistant/config.py
+++ b/assistants/codespace-assistant/assistant/config.py
@@ -126,7 +126,7 @@ class AssistantConfigModel(BaseModel):
         AzureOpenAIClientConfigModel | OpenAIClientConfigModel,
         Field(
             title="OpenAI Reasoning Model Configuration",
-            description="Configuration for the reasoning model, such as o1-preview, o1-mini, etc.",
+            description="Configuration for the reasoning model, such as o1, o1-preview, o1-mini, etc.",
             discriminator="ai_service_type",
             default=AzureOpenAIClientConfigModel.model_construct(),
         ),
diff --git a/assistants/codespace-assistant/assistant/extensions/tools/__mcp_server_configs.py b/assistants/codespace-assistant/assistant/extensions/tools/__mcp_server_configs.py
index e805e197..8ad87138 100644
--- a/assistants/codespace-assistant/assistant/extensions/tools/__mcp_server_configs.py
+++ b/assistants/codespace-assistant/assistant/extensions/tools/__mcp_server_configs.py
@@ -21,15 +21,12 @@
         prompt=dedent("""
             Follow these steps for each interaction:
 
-            1. User Identification:
-            - You should assume that you are interacting with default_user
-            - If you have not identified default_user, proactively try to do so.
-
-            2. Memory Retrieval:
-            - Always begin your chat by saying only "Remembering..." and retrieve all relevant information from your knowledge graph
+            1. Memory Retrieval:
+            - Always begin your chat by saying only "Remembering..." and retrieve all relevant information
+              from your knowledge graph
             - Always refer to your knowledge graph as your "memory"
 
-            3. Memory
+            2. Memory
             - While conversing with the user, be attentive to any new information that falls into these categories:
                 a) Basic Identity (age, gender, location, job title, education level, etc.)
                 b) Behaviors (interests, habits, etc.)
@@ -37,16 +34,21 @@
                 d) Goals (goals, targets, aspirations, etc.)
                 e) Relationships (personal and professional relationships up to 3 degrees of separation)
 
-            4. Memory Update:
+            3. Memory Update:
             - If any new information was gathered during the interaction, update your memory as follows:
                 a) Create entities for recurring organizations, people, and significant events
                 b) Connect them to the current entities using relations
                 b) Store facts about them as observations
         """),
     ),
-    MCPServerConfig(
-        name="Web Research MCP Server",
-        command="npx",
-        args=["-y", "@mzxrai/mcp-webresearch@latest"],
-    ),
+    # MCPServerConfig(
+    #     name="Sequential Thinking MCP Server",
+    #     command="npx",
+    #     args=["-y", "@modelcontextprotocol/server-sequential-thinking"],
+    # ),
+    # MCPServerConfig(
+    #     name="Web Research MCP Server",
+    #     command="npx",
+    #     args=["-y", "@mzxrai/mcp-webresearch@latest"],
+    # ),
 ]
diff --git a/assistants/codespace-assistant/assistant/response/completion_handler.py b/assistants/codespace-assistant/assistant/response/completion_handler.py
index 217f7de3..d9500a15 100644
--- a/assistants/codespace-assistant/assistant/response/completion_handler.py
+++ b/assistants/codespace-assistant/assistant/response/completion_handler.py
@@ -41,7 +41,7 @@ async def handle_completion(
     context: ConversationContext,
     config: AssistantConfigModel,
     silence_token: str,
-    method_metadata_key: str,
+    metadata_key: str,
     response_start_time: float,
 ) -> StepResult:
     # helper function for handling errors
@@ -90,7 +90,7 @@ async def handle_error(error_message: str) -> StepResult:
         step_result.metadata,
         {
             "debug": {
-                method_metadata_key: {
+                metadata_key: {
                     "response": completion.model_dump() if completion else "[no response from openai]",
                 },
             },
@@ -163,7 +163,7 @@ async def handle_error(error_message: str) -> StepResult:
                     mcp_sessions,
                     tool_call,
                     mcp_tools,
-                    f"{method_metadata_key}:request:tool_call_{tool_call_count}",
+                    f"{metadata_key}:request:tool_call_{tool_call_count}",
                 )
             except Exception as e:
                 logger.exception(f"Error handling tool call: {e}")
diff --git a/assistants/codespace-assistant/assistant/response/response.py b/assistants/codespace-assistant/assistant/response/response.py
index edd7fb61..e8fdf82d 100644
--- a/assistants/codespace-assistant/assistant/response/response.py
+++ b/assistants/codespace-assistant/assistant/response/response.py
@@ -54,6 +54,7 @@ async def respond_to_conversation(
 
         # Initialize a loop control variable
         max_steps = config.extensions_config.tools.max_steps
+        encountered_error = False
         completed_within_max_steps = False
         step_count = 0
 
@@ -69,14 +70,19 @@ async def respond_to_conversation(
                 context=context,
                 config=config,
                 metadata=metadata,
+                metadata_key=f"respond_to_conversation:step_{step_count}",
             )
 
+            if step_result.status == "error":
+                encountered_error = True
+                break
+
             if step_result.status == "final":
                 completed_within_max_steps = True
                 break
 
         # If the conversation did not complete within the maximum number of steps, send a message to the user
-        if not completed_within_max_steps:
+        if not completed_within_max_steps and not encountered_error:
             await context.send_messages(
                 NewConversationMessage(
                     content=config.extensions_config.tools.max_steps_truncation_message,
diff --git a/assistants/codespace-assistant/assistant/response/step_handler.py b/assistants/codespace-assistant/assistant/response/step_handler.py
index 8f642e04..20e7bfa0 100644
--- a/assistants/codespace-assistant/assistant/response/step_handler.py
+++ b/assistants/codespace-assistant/assistant/response/step_handler.py
@@ -36,11 +36,23 @@ async def next_step(
     context: ConversationContext,
     config: AssistantConfigModel,
     metadata: dict[str, Any],
+    metadata_key: str,
 ) -> StepResult:
     step_result = StepResult(status="continue", metadata=metadata.copy())
 
     # helper function for handling errors
-    async def handle_error(error_message: str) -> StepResult:
+    async def handle_error(error_message: str, error_debug: dict[str, Any] | None = None) -> StepResult:
+        if error_debug is not None:
+            deepmerge.always_merger.merge(
+                step_result.metadata,
+                {
+                    "debug": {
+                        metadata_key: {
+                            "error": error_debug,
+                        },
+                    },
+                },
+            )
         await context.send_messages(
             NewConversationMessage(
                 content=error_message,
@@ -63,9 +75,6 @@ async def handle_error(error_message: str) -> StepResult:
     # )
     # reasoning_request_config = config.reasoning_ai_client_config.request_config
 
-    # Define the metadata key for any metadata created within this method
-    method_metadata_key = "respond_to_conversation"
-
     # Track the start time of the response generation
     response_start_time = time.time()
 
@@ -92,7 +101,7 @@ async def handle_error(error_message: str) -> StepResult:
         step_result.metadata,
         {
             "debug": {
-                method_metadata_key: {
+                metadata_key: {
                     "request": {
                         "model": generative_request_config.model,
                         "messages": chat_message_params,
@@ -111,12 +120,22 @@ async def handle_error(error_message: str) -> StepResult:
 
         except Exception as e:
             logger.exception(f"exception occurred calling openai chat completion: {e}")
+            deepmerge.always_merger.merge(
+                step_result.metadata,
+                {
+                    "debug": {
+                        metadata_key: {
+                            "error": str(e),
+                        },
+                    },
+                },
+            )
             await context.send_messages(
                 NewConversationMessage(
                     content="An error occurred while calling the OpenAI API. Is it configured correctly?"
                     " View the debug inspector for more information.",
                     message_type=MessageType.notice,
-                    metadata={method_metadata_key: {"error": str(e)}},
+                    metadata=step_result.metadata,
                 )
             )
             step_result.status = "error"
@@ -133,7 +152,7 @@ async def handle_error(error_message: str) -> StepResult:
         context,
         config,
         silence_token,
-        method_metadata_key,
+        metadata_key,
         response_start_time,
     )
 
diff --git a/assistants/codespace-assistant/assistant/response/utils/openai_utils.py b/assistants/codespace-assistant/assistant/response/utils/openai_utils.py
index 320e5daf..ff41a7ea 100644
--- a/assistants/codespace-assistant/assistant/response/utils/openai_utils.py
+++ b/assistants/codespace-assistant/assistant/response/utils/openai_utils.py
@@ -128,6 +128,7 @@ def convert_mcp_tools_to_openai_tools(mcp_tools: List[Tool] | None) -> List[Chat
                             "properties": {
                                 "aiContext": aiContext,
                             },
+                            "required": ["aiContext"],
                         },
                     ),
                 ),
diff --git a/assistants/codespace-assistant/pyproject.toml b/assistants/codespace-assistant/pyproject.toml
index 3aab7978..02727513 100644
--- a/assistants/codespace-assistant/pyproject.toml
+++ b/assistants/codespace-assistant/pyproject.toml
@@ -15,8 +15,9 @@ dependencies = [
     "html2docx>=1.6.0",
     "markdown>=3.6",
     "mcp>=1.2.0",
-    "openai>=1.3.9",
+    "openai>=1.60.2",
     "openai-client>=0.1.0",
+    "tiktoken>=0.8.0",
 ]
 
 [tool.hatch.build.targets.wheel]
diff --git a/assistants/codespace-assistant/uv.lock b/assistants/codespace-assistant/uv.lock
index d38cd8e7..61b170bc 100644
--- a/assistants/codespace-assistant/uv.lock
+++ b/assistants/codespace-assistant/uv.lock
@@ -95,7 +95,7 @@ wheels = [
 
 [[package]]
 name = "anthropic"
-version = "0.44.0"
+version = "0.45.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
@@ -106,9 +106,9 @@ dependencies = [
     { name = "sniffio" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/eb/34/ed394012684f7d6e36bb36c8b7c82b438f0ef189d2afd3d0090b85801211/anthropic-0.44.0.tar.gz", hash = "sha256:dc5c91c8b0463f97513d2e79350511ef295a56910bac4fbbe9491016c71f2ef0", size = 196065 }
+sdist = { url = "https://files.pythonhosted.org/packages/15/74/2b2485fc120da834c0c5be07462541ec082e9fa8851d845f2587e480535a/anthropic-0.45.2.tar.gz", hash = "sha256:32a18b9ecd12c91b2be4cae6ca2ab46a06937b5aa01b21308d97a6d29794fb5e", size = 200901 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/d3/ad/c3c7d199eedc0b6d4621deed8dc1ed252ce399400cd76f1da098f1f50e56/anthropic-0.44.0-py3-none-any.whl", hash = "sha256:7087ccfc8ed7b164f971e094495cd3aeabac1e435fa393480cc146c87946c21c", size = 208634 },
+    { url = "https://files.pythonhosted.org/packages/74/86/e81814e542d1eaeec84d2312bec93a99b9ef1d78d9bfae1fc5dd74abdf15/anthropic-0.45.2-py3-none-any.whl", hash = "sha256:ecd746f7274451dfcb7e1180571ead624c7e1195d1d46cb7c70143d2aedb4d35", size = 222797 },
 ]
 
 [[package]]
@@ -221,7 +221,7 @@ requires-dist = [
     { name = "assistant-drive", editable = "../../libraries/python/assistant-drive" },
     { name = "assistant-drive", marker = "extra == 'attachments'", editable = "../../libraries/python/assistant-drive" },
     { name = "docx2txt", marker = "extra == 'attachments'", specifier = ">=0.8" },
-    { name = "openai", specifier = ">=1.51.2" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "openai-client", editable = "../../libraries/python/openai-client" },
     { name = "pdfplumber", marker = "extra == 'attachments'", specifier = ">=0.11.2" },
     { name = "requests-sse", specifier = ">=0.3.2" },
@@ -237,11 +237,11 @@ dev = [
 
 [[package]]
 name = "attrs"
-version = "24.3.0"
+version = "25.1.0"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/48/c8/6260f8ccc11f0917360fc0da435c5c9c7504e3db174d5a12a1494887b045/attrs-24.3.0.tar.gz", hash = "sha256:8f5c07333d543103541ba7be0e2ce16eeee8130cb0b3f9238ab904ce1e85baff", size = 805984 }
+sdist = { url = "https://files.pythonhosted.org/packages/49/7c/fdf464bcc51d23881d110abd74b512a42b3d5d376a55a831b44c603ae17f/attrs-25.1.0.tar.gz", hash = "sha256:1c97078a80c814273a76b2a298a932eb681c87415c11dee0a6921de7f1b02c3e", size = 810562 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/89/aa/ab0f7891a01eeb2d2e338ae8fecbe57fcebea1a24dbb64d45801bfab481d/attrs-24.3.0-py3-none-any.whl", hash = "sha256:ac96cd038792094f438ad1f6ff80837353805ac950cd2aa0e0625ef19850c308", size = 63397 },
+    { url = "https://files.pythonhosted.org/packages/fc/30/d4986a882011f9df997a55e6becd864812ccfcd821d64aac8570ee39f719/attrs-25.1.0-py3-none-any.whl", hash = "sha256:c75a69e28a550a7e93789579c22aa26b0f5b83b75dc4e08fe092980051e1090a", size = 63152 },
 ]
 
 [[package]]
@@ -431,6 +431,7 @@ dependencies = [
     { name = "mcp" },
     { name = "openai" },
     { name = "openai-client" },
+    { name = "tiktoken" },
 ]
 
 [package.dev-dependencies]
@@ -449,8 +450,9 @@ requires-dist = [
     { name = "html2docx", specifier = ">=1.6.0" },
     { name = "markdown", specifier = ">=3.6" },
     { name = "mcp", specifier = ">=1.2.0" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "openai-client", editable = "../../libraries/python/openai-client" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
 ]
 
 [package.metadata.requires-dev]
@@ -482,7 +484,7 @@ requires-dist = [
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "semantic-workbench-assistant", editable = "../../libraries/python/semantic-workbench-assistant" },
 ]
 
@@ -601,16 +603,16 @@ dev = [{ name = "pyright", specifier = ">=1.1.389" }]
 
 [[package]]
 name = "fastapi"
-version = "0.115.6"
+version = "0.115.7"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "pydantic" },
     { name = "starlette" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/93/72/d83b98cd106541e8f5e5bfab8ef2974ab45a62e8a6c5b5e6940f26d2ed4b/fastapi-0.115.6.tar.gz", hash = "sha256:9ec46f7addc14ea472958a96aae5b5de65f39721a46aaf5705c480d9a8b76654", size = 301336 }
+sdist = { url = "https://files.pythonhosted.org/packages/a2/f5/3f921e59f189e513adb9aef826e2841672d50a399fead4e69afdeb808ff4/fastapi-0.115.7.tar.gz", hash = "sha256:0f106da6c01d88a6786b3248fb4d7a940d071f6f488488898ad5d354b25ed015", size = 293177 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/52/b3/7e4df40e585df024fac2f80d1a2d579c854ac37109675db2b0cc22c0bb9e/fastapi-0.115.6-py3-none-any.whl", hash = "sha256:e9240b29e36fa8f4bb7290316988e90c381e5092e0cbe84e7818cc3713bcf305", size = 94843 },
+    { url = "https://files.pythonhosted.org/packages/e6/7f/bbd4dcf0faf61bc68a01939256e2ed02d681e9334c1a3cef24d5f77aba9f/fastapi-0.115.7-py3-none-any.whl", hash = "sha256:eb6a8c8bf7f26009e8147111ff15b5177a0e19bb4a45bc3486ab14804539d21e", size = 94777 },
 ]
 
 [package.optional-dependencies]
@@ -1000,7 +1002,7 @@ wheels = [
 
 [[package]]
 name = "mcp"
-version = "1.2.0"
+version = "1.2.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
@@ -1012,9 +1014,9 @@ dependencies = [
     { name = "starlette" },
     { name = "uvicorn" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/ab/a5/b08dc846ebedae9f17ced878e6975826e90e448cd4592f532f6a88a925a7/mcp-1.2.0.tar.gz", hash = "sha256:2b06c7ece98d6ea9e6379caa38d74b432385c338fb530cb82e2c70ea7add94f5", size = 102973 }
+sdist = { url = "https://files.pythonhosted.org/packages/fc/30/51e4555826126e3954fa2ab1e934bf74163c5fe05e98f38ca4d0f8abbf63/mcp-1.2.1.tar.gz", hash = "sha256:c9d43dbfe943aa1530e2be8f54b73af3ebfb071243827b4483d421684806cb45", size = 103968 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/af/84/fca78f19ac8ce6c53ba416247c71baa53a9e791e98d3c81edbc20a77d6d1/mcp-1.2.0-py3-none-any.whl", hash = "sha256:1d0e77d8c14955a5aea1f5aa1f444c8e531c09355c829b20e42f7a142bc0755f", size = 66468 },
+    { url = "https://files.pythonhosted.org/packages/4c/0d/6770742a84c8aa1d36c0d628896a380584c5759612e66af7446af07d8775/mcp-1.2.1-py3-none-any.whl", hash = "sha256:579bf9c9157850ebb1344f3ca6f7a3021b0123c44c9f089ef577a7062522f0fd", size = 66453 },
 ]
 
 [[package]]
@@ -1118,7 +1120,7 @@ wheels = [
 
 [[package]]
 name = "openai"
-version = "1.60.0"
+version = "1.60.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
@@ -1130,9 +1132,9 @@ dependencies = [
     { name = "tqdm" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/d4/2d/9bdf4435d7669b4d027d6d69b4ac82f6be76153d9e90d3155d4224626a29/openai-1.60.0.tar.gz", hash = "sha256:7fa536cd4b644718645b874d2706e36dbbef38b327e42ca0623275da347ee1a9", size = 347844 }
+sdist = { url = "https://files.pythonhosted.org/packages/08/ae/8d9706b8ff2363287b4a8807de2dd29cdbdad5424e9d05d345df724320f5/openai-1.60.2.tar.gz", hash = "sha256:a8f843e10f2855713007f491d96afb2694b11b5e02cb97c7d01a0be60bc5bb51", size = 348185 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/c0/53/782008d94f5f3141795e65bd7f87afaebb97e7516342299c1b1a08d5aaf8/openai-1.60.0-py3-none-any.whl", hash = "sha256:df06c43be8018274980ac363da07d4b417bd835ead1c66e14396f6f15a0d5dda", size = 456109 },
+    { url = "https://files.pythonhosted.org/packages/e5/5a/d5474ca67a547dde9b87b5bc8a8f90eadf29f523d410f2ba23d63c9b82ec/openai-1.60.2-py3-none-any.whl", hash = "sha256:993bd11b96900b9098179c728026f016b4982ded7ee30dfcf4555eab1171fff9", size = 456107 },
 ]
 
 [[package]]
@@ -1159,11 +1161,11 @@ requires-dist = [
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
     { name = "events", editable = "../../libraries/python/events" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "pillow", specifier = ">=11.0.0" },
     { name = "python-liquid", specifier = ">=1.12.1" },
     { name = "semantic-workbench-assistant", editable = "../../libraries/python/semantic-workbench-assistant" },
-    { name = "tiktoken", specifier = ">=0.7.0" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
 ]
 
 [package.metadata.requires-dev]
@@ -1337,16 +1339,16 @@ wheels = [
 
 [[package]]
 name = "pydantic"
-version = "2.10.5"
+version = "2.10.6"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "annotated-types" },
     { name = "pydantic-core" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/6a/c7/ca334c2ef6f2e046b1144fe4bb2a5da8a4c574e7f2ebf7e16b34a6a2fa92/pydantic-2.10.5.tar.gz", hash = "sha256:278b38dbbaec562011d659ee05f63346951b3a248a6f3642e1bc68894ea2b4ff", size = 761287 }
+sdist = { url = "https://files.pythonhosted.org/packages/b7/ae/d5220c5c52b158b1de7ca89fc5edb72f304a70a4c540c84c8844bf4008de/pydantic-2.10.6.tar.gz", hash = "sha256:ca5daa827cce33de7a42be142548b0096bf05a7e7b365aebfa5f8eeec7128236", size = 761681 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/58/26/82663c79010b28eddf29dcdd0ea723439535fa917fce5905885c0e9ba562/pydantic-2.10.5-py3-none-any.whl", hash = "sha256:4dd4e322dbe55472cb7ca7e73f4b63574eecccf2835ffa2af9021ce113c83c53", size = 431426 },
+    { url = "https://files.pythonhosted.org/packages/f4/3c/8cc1cc84deffa6e25d2d0c688ebb80635dfdbf1dbea3e30c541c8cf4d860/pydantic-2.10.6-py3-none-any.whl", hash = "sha256:427d664bf0b8a2b34ff5dd0f5a18df00591adcee7198fbd71981054cef37b584", size = 431696 },
 ]
 
 [[package]]
@@ -1791,14 +1793,14 @@ wheels = [
 
 [[package]]
 name = "starlette"
-version = "0.41.3"
+version = "0.45.3"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/1a/4c/9b5764bd22eec91c4039ef4c55334e9187085da2d8a2df7bd570869aae18/starlette-0.41.3.tar.gz", hash = "sha256:0e4ab3d16522a255be6b28260b938eae2482f98ce5cc934cb08dce8dc3ba5835", size = 2574159 }
+sdist = { url = "https://files.pythonhosted.org/packages/ff/fb/2984a686808b89a6781526129a4b51266f678b2d2b97ab2d325e56116df8/starlette-0.45.3.tar.gz", hash = "sha256:2cbcba2a75806f8a41c722141486f37c28e30a0921c5f6fe4346cb0dcee1302f", size = 2574076 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/96/00/2b325970b3060c7cecebab6d295afe763365822b1306a12eeab198f74323/starlette-0.41.3-py3-none-any.whl", hash = "sha256:44cedb2b7c77a9de33a8b74b2b90e9f50d11fcf25d8270ea525ad71a25374ff7", size = 73225 },
+    { url = "https://files.pythonhosted.org/packages/d9/61/f2b52e107b1fc8944b33ef56bf6ac4ebbe16d91b94d2b87ce013bf63fb84/starlette-0.45.3-py3-none-any.whl", hash = "sha256:dfb6d332576f136ec740296c7e8bb8c8a7125044e7c6da30744718880cdd059d", size = 71507 },
 ]
 
 [[package]]
diff --git a/assistants/explorer-assistant/.vscode/launch.json b/assistants/explorer-assistant/.vscode/launch.json
index 682ee10e..7457d1bb 100644
--- a/assistants/explorer-assistant/.vscode/launch.json
+++ b/assistants/explorer-assistant/.vscode/launch.json
@@ -8,6 +8,7 @@
       "cwd": "${workspaceFolder}",
       "module": "semantic_workbench_assistant.start",
       "consoleTitle": "${workspaceFolderBasename}"
+      // "justMyCode": false, // Set to false to debug external libraries
     }
   ]
 }
diff --git a/assistants/explorer-assistant/assistant/response/response_openai.py b/assistants/explorer-assistant/assistant/response/response_openai.py
index e4851540..f72a8e4c 100644
--- a/assistants/explorer-assistant/assistant/response/response_openai.py
+++ b/assistants/explorer-assistant/assistant/response/response_openai.py
@@ -10,7 +10,9 @@
 from assistant_extensions.artifacts import ArtifactsExtension
 from openai.types.chat import (
     ChatCompletion,
+    ChatCompletionDeveloperMessageParam,
     ChatCompletionMessageParam,
+    ChatCompletionUserMessageParam,
     ParsedChatCompletion,
 )
 from semantic_workbench_api_model.workbench_model import (
@@ -109,22 +111,34 @@ async def get_response(
         async with openai_client.create_client(self.service_config) as client:
             try:
                 if self.request_config.is_reasoning_model:
-                    # convert all messages that use system role to user role as reasoning models do not support system role
-                    chat_message_params = [
-                        {
-                            "role": "user",
-                            "content": message["content"],
-                        }
-                        if message["role"] == "system"
-                        else message
-                        for message in chat_message_params
-                    ]
+                    # reasoning models do not support system messages, so replace them with appropriate role
+                    if self.request_config.model != "o1-preview":
+                        chat_message_params = [
+                            ChatCompletionDeveloperMessageParam({
+                                "role": "developer",
+                                "content": message["content"],
+                            })
+                            if message["role"] == "system"
+                            else message
+                            for message in chat_message_params
+                        ]
+                    else:
+                        chat_message_params = [
+                            ChatCompletionUserMessageParam({
+                                "role": "user",
+                                "content": message["content"],
+                            })
+                            if message["role"] == "system"
+                            else message
+                            for message in chat_message_params
+                        ]
 
                     # for reasoning models, use max_completion_tokens instead of max_tokens
                     completion = await client.chat.completions.create(
                         messages=chat_message_params,
                         model=self.request_config.model,
                         max_completion_tokens=self.request_config.response_tokens,
+                        reasoning_effort=self.request_config.reasoning_effort,
                     )
 
                     response_result.content = completion.choices[0].message.content
@@ -171,6 +185,7 @@ async def get_response(
                             messages=chat_message_params,
                             model=self.request_config.model,
                             max_completion_tokens=self.request_config.response_tokens,
+                            reasoning_effort=self.request_config.reasoning_effort,
                         )
                     else:
                         completion = await client.chat.completions.create(
diff --git a/assistants/explorer-assistant/pyproject.toml b/assistants/explorer-assistant/pyproject.toml
index 1279b48d..0111451e 100644
--- a/assistants/explorer-assistant/pyproject.toml
+++ b/assistants/explorer-assistant/pyproject.toml
@@ -14,7 +14,7 @@ dependencies = [
     "deepmerge>=2.0",
     "html2docx>=1.6.0",
     "markdown>=3.6",
-    "openai>=1.3.9",
+    "openai>=1.60.2",
     "openai-client>=0.1.0",
 ]
 
diff --git a/assistants/explorer-assistant/uv.lock b/assistants/explorer-assistant/uv.lock
index f7a63665..8a6f0581 100644
--- a/assistants/explorer-assistant/uv.lock
+++ b/assistants/explorer-assistant/uv.lock
@@ -1,23 +1,18 @@
 version = 1
 requires-python = ">=3.11"
-resolution-markers = [
-    "python_full_version < '3.12'",
-    "python_full_version == '3.12.*'",
-    "python_full_version >= '3.13'",
-]
 
 [[package]]
 name = "aiohappyeyeballs"
-version = "2.4.3"
+version = "2.4.4"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/bc/69/2f6d5a019bd02e920a3417689a89887b39ad1e350b562f9955693d900c40/aiohappyeyeballs-2.4.3.tar.gz", hash = "sha256:75cf88a15106a5002a8eb1dab212525c00d1f4c0fa96e551c9fbe6f09a621586", size = 21809 }
+sdist = { url = "https://files.pythonhosted.org/packages/7f/55/e4373e888fdacb15563ef6fa9fa8c8252476ea071e96fb46defac9f18bf2/aiohappyeyeballs-2.4.4.tar.gz", hash = "sha256:5fdd7d87889c63183afc18ce9271f9b0a7d32c2303e394468dd45d514a757745", size = 21977 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/f7/d8/120cd0fe3e8530df0539e71ba9683eade12cae103dd7543e50d15f737917/aiohappyeyeballs-2.4.3-py3-none-any.whl", hash = "sha256:8a7a83727b2756f394ab2895ea0765a0a8c475e3c71e98d43d76f22b4b435572", size = 14742 },
+    { url = "https://files.pythonhosted.org/packages/b9/74/fbb6559de3607b3300b9be3cc64e97548d55678e44623db17820dbd20002/aiohappyeyeballs-2.4.4-py3-none-any.whl", hash = "sha256:a980909d50efcd44795c4afeca523296716d50cd756ddca6af8c65b996e27de8", size = 14756 },
 ]
 
 [[package]]
 name = "aiohttp"
-version = "3.11.6"
+version = "3.11.11"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "aiohappyeyeballs" },
@@ -28,65 +23,65 @@ dependencies = [
     { name = "propcache" },
     { name = "yarl" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/d5/66/a967a2e9ceab12b6970ca5be3bccc9cf13fed4acfabe2c66de3d75599185/aiohttp-3.11.6.tar.gz", hash = "sha256:fd9f55c1b51ae1c20a1afe7216a64a88d38afee063baa23c7fce03757023c999", size = 7666498 }
-wheels = [
-    { url = "https://files.pythonhosted.org/packages/70/fe/32fc7c6e0a0f2f5b319b144aa7b83e631f9dd7c4b2378ccd4a4f89e273a8/aiohttp-3.11.6-cp311-cp311-macosx_10_9_universal2.whl", hash = "sha256:26ac4c960ea8debf557357a172b3ef201f2236a462aefa1bc17683a75483e518", size = 706721 },
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diff --git a/assistants/guided-conversation-assistant/pyproject.toml b/assistants/guided-conversation-assistant/pyproject.toml
index 15ea01cd..16215ac3 100644
--- a/assistants/guided-conversation-assistant/pyproject.toml
+++ b/assistants/guided-conversation-assistant/pyproject.toml
@@ -10,9 +10,9 @@ dependencies = [
     "docx2txt>=0.8",
     "html2docx>=1.6.0",
     "markdown>=3.6",
-    "openai>=1.3.9",
+    "openai>=1.60.2",
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-    "tiktoken>=0.7.0",
+    "tiktoken>=0.8.0",
     "semantic-workbench-assistant>=0.1.0",
     "content-safety>=0.1.0",
     "semantic-kernel>=1.11.0",
@@ -34,9 +34,7 @@ requires = ["hatchling"]
 build-backend = "hatchling.build"
 
 [dependency-groups]
-dev = [
-    "pyright>=1.1.389",
-]
+dev = ["pyright>=1.1.389"]
 
 [tool.pyright]
 exclude = ["venv", ".venv"]
diff --git a/assistants/guided-conversation-assistant/uv.lock b/assistants/guided-conversation-assistant/uv.lock
index cbab48e5..58cbb9c5 100644
--- a/assistants/guided-conversation-assistant/uv.lock
+++ b/assistants/guided-conversation-assistant/uv.lock
@@ -201,12 +201,12 @@ requires-dist = [
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     { name = "markdown", specifier = ">=3.6" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
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     { name = "pdfplumber", specifier = ">=0.11.2" },
     { name = "semantic-kernel", specifier = ">=1.11.0" },
     { name = "semantic-workbench-assistant", editable = "../../libraries/python/semantic-workbench-assistant" },
-    { name = "tiktoken", specifier = ">=0.7.0" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
 ]
 
 [package.metadata.requires-dev]
@@ -266,7 +266,7 @@ requires-dist = [
     { name = "assistant-drive", editable = "../../libraries/python/assistant-drive" },
     { name = "assistant-drive", marker = "extra == 'attachments'", editable = "../../libraries/python/assistant-drive" },
     { name = "docx2txt", marker = "extra == 'attachments'", specifier = ">=0.8" },
-    { name = "openai", specifier = ">=1.51.2" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "openai-client", editable = "../../libraries/python/openai-client" },
     { name = "pdfplumber", marker = "extra == 'attachments'", specifier = ">=0.11.2" },
     { name = "requests-sse", specifier = ">=0.3.2" },
@@ -453,7 +453,7 @@ name = "click"
 version = "8.1.7"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
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     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "semantic-workbench-assistant", editable = "../../libraries/python/semantic-workbench-assistant" },
 ]
 
@@ -1214,7 +1214,7 @@ wheels = [
 
 [[package]]
 name = "openai"
-version = "1.55.3"
+version = "1.60.2"
 source = { registry = "https://pypi.org/simple" }
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     { name = "azure-identity", specifier = ">=1.17.1" },
     { name = "events", editable = "../../libraries/python/events" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
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-    { name = "tiktoken", specifier = ">=0.7.0" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
 ]
 
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 version = "2.10.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "pywin32", marker = "platform_system == 'Windows'" },
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diff --git a/assistants/prospector-assistant/pyproject.toml b/assistants/prospector-assistant/pyproject.toml
index afbf3706..b03887a8 100644
--- a/assistants/prospector-assistant/pyproject.toml
+++ b/assistants/prospector-assistant/pyproject.toml
@@ -14,7 +14,7 @@ dependencies = [
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     "markdown>=3.6",
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+    "openai>=1.60.2",
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diff --git a/assistants/prospector-assistant/uv.lock b/assistants/prospector-assistant/uv.lock
index e4035b92..aeb5fc56 100644
--- a/assistants/prospector-assistant/uv.lock
+++ b/assistants/prospector-assistant/uv.lock
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 version = "2.10.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
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-    { name = "colorama", marker = "platform_system == 'Windows'" },
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diff --git a/assistants/skill-assistant/pyproject.toml b/assistants/skill-assistant/pyproject.toml
index 6212c77b..af3bd080 100644
--- a/assistants/skill-assistant/pyproject.toml
+++ b/assistants/skill-assistant/pyproject.toml
@@ -15,7 +15,7 @@ dependencies = [
     "form-filler-skill>=0.1.0",
     "guided-conversation-skill>=0.1.0",
     "openai-client>=0.1.0",
-    "openai>=1.3.9",
+    "openai>=1.60.2",
     "posix-skill>=0.1.0",
     "semantic-workbench-assistant>=0.1.0",
     "bs4>=0.0.2",
diff --git a/assistants/skill-assistant/uv.lock b/assistants/skill-assistant/uv.lock
index 2884ea4d..3f41c9ae 100644
--- a/assistants/skill-assistant/uv.lock
+++ b/assistants/skill-assistant/uv.lock
@@ -216,7 +216,7 @@ requires-dist = [
     { name = "content-safety", editable = "../../libraries/python/content-safety" },
     { name = "form-filler-skill", editable = "../../libraries/python/skills/skills/form-filler-skill" },
     { name = "guided-conversation-skill", editable = "../../libraries/python/skills/skills/guided-conversation-skill" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "openai-client", editable = "../../libraries/python/openai-client" },
     { name = "posix-skill", editable = "../../libraries/python/skills/skills/posix-skill" },
     { name = "semantic-workbench-assistant", editable = "../../libraries/python/semantic-workbench-assistant" },
@@ -282,7 +282,7 @@ requires-dist = [
     { name = "assistant-drive", editable = "../../libraries/python/assistant-drive" },
     { name = "assistant-drive", marker = "extra == 'attachments'", editable = "../../libraries/python/assistant-drive" },
     { name = "docx2txt", marker = "extra == 'attachments'", specifier = ">=0.8" },
-    { name = "openai", specifier = ">=1.51.2" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "openai-client", editable = "../../libraries/python/openai-client" },
     { name = "pdfplumber", marker = "extra == 'attachments'", specifier = ">=0.11.2" },
     { name = "requests-sse", specifier = ">=0.3.2" },
@@ -508,7 +508,7 @@ name = "click"
 version = "8.1.7"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
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 sdist = { url = "https://files.pythonhosted.org/packages/96/d3/f04c7bfcf5c1862a2a5b845c6b2b360488cf47af55dfa79c98f6a6bf98b5/click-8.1.7.tar.gz", hash = "sha256:ca9853ad459e787e2192211578cc907e7594e294c7ccc834310722b41b9ca6de", size = 336121 }
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@@ -585,7 +585,7 @@ requires-dist = [
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     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
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@@ -987,7 +987,7 @@ name = "ipykernel"
 version = "6.29.5"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "appnope", marker = "platform_system == 'Darwin'" },
+    { name = "appnope", marker = "sys_platform == 'darwin'" },
     { name = "comm" },
     { name = "debugpy" },
     { name = "ipython" },
@@ -1346,7 +1346,7 @@ wheels = [
 
 [[package]]
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+version = "1.60.2"
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@@ -1358,9 +1358,9 @@ dependencies = [
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+sdist = { url = "https://files.pythonhosted.org/packages/08/ae/8d9706b8ff2363287b4a8807de2dd29cdbdad5424e9d05d345df724320f5/openai-1.60.2.tar.gz", hash = "sha256:a8f843e10f2855713007f491d96afb2694b11b5e02cb97c7d01a0be60bc5bb51", size = 348185 }
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@@ -1387,11 +1387,11 @@ requires-dist = [
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     { name = "azure-identity", specifier = ">=1.17.1" },
     { name = "events", editable = "../../libraries/python/events" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "pillow", specifier = ">=11.0.0" },
     { name = "python-liquid", specifier = ">=1.12.1" },
     { name = "semantic-workbench-assistant", editable = "../../libraries/python/semantic-workbench-assistant" },
-    { name = "tiktoken", specifier = ">=0.7.0" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
 ]
 
 [package.metadata.requires-dev]
@@ -1520,7 +1520,7 @@ name = "portalocker"
 version = "2.10.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "pywin32", marker = "platform_system == 'Windows'" },
+    { name = "pywin32", marker = "sys_platform == 'win32'" },
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 sdist = { url = "https://files.pythonhosted.org/packages/ed/d3/c6c64067759e87af98cc668c1cc75171347d0f1577fab7ca3749134e3cd4/portalocker-2.10.1.tar.gz", hash = "sha256:ef1bf844e878ab08aee7e40184156e1151f228f103aa5c6bd0724cc330960f8f", size = 40891 }
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@@ -2240,7 +2240,7 @@ requires-dist = [
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     { name = "requests", specifier = ">=2.32.0" },
-    { name = "tiktoken", specifier = ">=0.7.0" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
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 [package.metadata.requires-dev]
@@ -2348,7 +2348,7 @@ name = "tqdm"
 version = "4.67.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
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 sdist = { url = "https://files.pythonhosted.org/packages/a8/4b/29b4ef32e036bb34e4ab51796dd745cdba7ed47ad142a9f4a1eb8e0c744d/tqdm-4.67.1.tar.gz", hash = "sha256:f8aef9c52c08c13a65f30ea34f4e5aac3fd1a34959879d7e59e63027286627f2", size = 169737 }
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diff --git a/examples/python/python-01-echo-bot/pyproject.toml b/examples/python/python-01-echo-bot/pyproject.toml
index d1de18ad..5ecd3400 100644
--- a/examples/python/python-01-echo-bot/pyproject.toml
+++ b/examples/python/python-01-echo-bot/pyproject.toml
@@ -5,7 +5,7 @@ description = "Example of a python Semantic Workbench assistant."
 authors = [{ name = "Semantic Workbench Team" }]
 readme = "README.md"
 requires-python = ">=3.11"
-dependencies = ["openai>=1.3.9", "semantic-workbench-assistant>=0.1.0"]
+dependencies = ["openai>=1.60.2", "semantic-workbench-assistant>=0.1.0"]
 
 [tool.uv]
 package = true
diff --git a/examples/python/python-01-echo-bot/uv.lock b/examples/python/python-01-echo-bot/uv.lock
index 8e092d81..e13d442a 100644
--- a/examples/python/python-01-echo-bot/uv.lock
+++ b/examples/python/python-01-echo-bot/uv.lock
@@ -55,7 +55,7 @@ dev = [
 
 [package.metadata]
 requires-dist = [
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "semantic-workbench-assistant", editable = "../../../libraries/python/semantic-workbench-assistant" },
 ]
 
@@ -85,7 +85,7 @@ name = "click"
 version = "8.1.7"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
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 sdist = { url = "https://files.pythonhosted.org/packages/96/d3/f04c7bfcf5c1862a2a5b845c6b2b360488cf47af55dfa79c98f6a6bf98b5/click-8.1.7.tar.gz", hash = "sha256:ca9853ad459e787e2192211578cc907e7594e294c7ccc834310722b41b9ca6de", size = 336121 }
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@@ -356,7 +356,7 @@ wheels = [
 
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 name = "openai"
-version = "1.51.0"
+version = "1.60.2"
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@@ -368,9 +368,9 @@ dependencies = [
     { name = "tqdm" },
     { name = "typing-extensions" },
 ]
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+sdist = { url = "https://files.pythonhosted.org/packages/08/ae/8d9706b8ff2363287b4a8807de2dd29cdbdad5424e9d05d345df724320f5/openai-1.60.2.tar.gz", hash = "sha256:a8f843e10f2855713007f491d96afb2694b11b5e02cb97c7d01a0be60bc5bb51", size = 348185 }
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+    { url = "https://files.pythonhosted.org/packages/e5/5a/d5474ca67a547dde9b87b5bc8a8f90eadf29f523d410f2ba23d63c9b82ec/openai-1.60.2-py3-none-any.whl", hash = "sha256:993bd11b96900b9098179c728026f016b4982ded7ee30dfcf4555eab1171fff9", size = 456107 },
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 [[package]]
@@ -633,7 +633,7 @@ name = "tqdm"
 version = "4.66.5"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/58/83/6ba9844a41128c62e810fddddd72473201f3eacde02046066142a2d96cc5/tqdm-4.66.5.tar.gz", hash = "sha256:e1020aef2e5096702d8a025ac7d16b1577279c9d63f8375b63083e9a5f0fcbad", size = 169504 }
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diff --git a/examples/python/python-02-simple-chatbot/pyproject.toml b/examples/python/python-02-simple-chatbot/pyproject.toml
index b268632b..23d914a3 100644
--- a/examples/python/python-02-simple-chatbot/pyproject.toml
+++ b/examples/python/python-02-simple-chatbot/pyproject.toml
@@ -6,8 +6,8 @@ authors = [{ name = "Semantic Workbench Team" }]
 readme = "README.md"
 requires-python = ">=3.11"
 dependencies = [
-    "openai>=1.3.9",
-    "tiktoken>=0.7.0",
+    "openai>=1.60.2",
+    "tiktoken>=0.8.0",
     "semantic-workbench-assistant>=0.1.0",
     "content-safety>=0.1.0",
     "openai-client>=0.1.0",
@@ -26,6 +26,4 @@ requires = ["hatchling"]
 build-backend = "hatchling.build"
 
 [dependency-groups]
-dev = [
-    "pyright>=1.1.389",
-]
+dev = ["pyright>=1.1.389"]
diff --git a/examples/python/python-02-simple-chatbot/uv.lock b/examples/python/python-02-simple-chatbot/uv.lock
index 95bce622..9875cacc 100644
--- a/examples/python/python-02-simple-chatbot/uv.lock
+++ b/examples/python/python-02-simple-chatbot/uv.lock
@@ -188,10 +188,10 @@ dev = [
 [package.metadata]
 requires-dist = [
     { name = "content-safety", editable = "../../../libraries/python/content-safety" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "openai-client", editable = "../../../libraries/python/openai-client" },
     { name = "semantic-workbench-assistant", editable = "../../../libraries/python/semantic-workbench-assistant" },
-    { name = "tiktoken", specifier = ">=0.7.0" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
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 [package.metadata.requires-dev]
@@ -251,7 +251,7 @@ requires-dist = [
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     { name = "assistant-drive", marker = "extra == 'attachments'", editable = "../../../libraries/python/assistant-drive" },
     { name = "docx2txt", marker = "extra == 'attachments'", specifier = ">=0.8" },
-    { name = "openai", specifier = ">=1.51.2" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "openai-client", editable = "../../../libraries/python/openai-client" },
     { name = "pdfplumber", marker = "extra == 'attachments'", specifier = ">=0.11.2" },
     { name = "requests-sse", specifier = ">=0.3.2" },
@@ -429,7 +429,7 @@ name = "click"
 version = "8.1.7"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
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 source = { registry = "https://pypi.org/simple" }
 dependencies = [
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 source = { registry = "https://pypi.org/simple" }
 dependencies = [
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diff --git a/examples/python/python-03-multimodel-chatbot/pyproject.toml b/examples/python/python-03-multimodel-chatbot/pyproject.toml
index 4984d4e9..62a323da 100644
--- a/examples/python/python-03-multimodel-chatbot/pyproject.toml
+++ b/examples/python/python-03-multimodel-chatbot/pyproject.toml
@@ -8,8 +8,8 @@ requires-python = ">=3.11"
 dependencies = [
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     "google-generativeai>=0.8.1",
-    "openai>=1.3.9",
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+    "tiktoken>=0.8.0",
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@@ -28,6 +28,4 @@ requires = ["hatchling"]
 build-backend = "hatchling.build"
 
 [dependency-groups]
-dev = [
-    "pyright>=1.1.389",
-]
+dev = ["pyright>=1.1.389"]
diff --git a/examples/python/python-03-multimodel-chatbot/uv.lock b/examples/python/python-03-multimodel-chatbot/uv.lock
index f080f307..ae49c1d2 100644
--- a/examples/python/python-03-multimodel-chatbot/uv.lock
+++ b/examples/python/python-03-multimodel-chatbot/uv.lock
@@ -192,10 +192,10 @@ requires-dist = [
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     { name = "semantic-workbench-assistant", editable = "../../../libraries/python/semantic-workbench-assistant" },
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     { name = "assistant-drive", marker = "extra == 'attachments'", editable = "../../../libraries/python/assistant-drive" },
     { name = "docx2txt", marker = "extra == 'attachments'", specifier = ">=0.8" },
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+    { name = "openai", specifier = ">=1.60.2" },
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@@ -442,7 +442,7 @@ name = "click"
 version = "8.1.7"
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 dependencies = [
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diff --git a/libraries/python/anthropic-client/uv.lock b/libraries/python/anthropic-client/uv.lock
index 3559fda8..68196873 100644
--- a/libraries/python/anthropic-client/uv.lock
+++ b/libraries/python/anthropic-client/uv.lock
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     { url = "https://files.pythonhosted.org/packages/ef/82/72403624f197af0db6bac4e58153bc9ac0e6020e57234115db9596eee85d/cryptography-44.0.0-cp39-abi3-manylinux_2_28_x86_64.whl", hash = "sha256:f53c2c87e0fb4b0c00fa9571082a057e37690a8f12233306161c8f4b819960b7", size = 4155160 },
     { url = "https://files.pythonhosted.org/packages/a2/cd/2f3c440913d4329ade49b146d74f2e9766422e1732613f57097fea61f344/cryptography-44.0.0-cp39-abi3-manylinux_2_34_aarch64.whl", hash = "sha256:9e6fc8a08e116fb7c7dd1f040074c9d7b51d74a8ea40d4df2fc7aa08b76b9e6c", size = 3932331 },
-    { url = "https://files.pythonhosted.org/packages/31/d9/90409720277f88eb3ab72f9a32bfa54acdd97e94225df699e7713e850bd4/cryptography-44.0.0-cp39-abi3-manylinux_2_34_x86_64.whl", hash = "sha256:9abcc2e083cbe8dde89124a47e5e53ec38751f0d7dfd36801008f316a127d7ba", size = 4165207 },
     { url = "https://files.pythonhosted.org/packages/7f/df/8be88797f0a1cca6e255189a57bb49237402b1880d6e8721690c5603ac23/cryptography-44.0.0-cp39-abi3-musllinux_1_2_aarch64.whl", hash = "sha256:d2436114e46b36d00f8b72ff57e598978b37399d2786fd39793c36c6d5cb1c64", size = 4017372 },
     { url = "https://files.pythonhosted.org/packages/af/36/5ccc376f025a834e72b8e52e18746b927f34e4520487098e283a719c205e/cryptography-44.0.0-cp39-abi3-musllinux_1_2_x86_64.whl", hash = "sha256:a01956ddfa0a6790d594f5b34fc1bfa6098aca434696a03cfdbe469b8ed79285", size = 4239657 },
     { url = "https://files.pythonhosted.org/packages/46/b0/f4f7d0d0bcfbc8dd6296c1449be326d04217c57afb8b2594f017eed95533/cryptography-44.0.0-cp39-abi3-win32.whl", hash = "sha256:eca27345e1214d1b9f9490d200f9db5a874479be914199194e746c893788d417", size = 2758672 },
@@ -964,7 +962,7 @@ wheels = [
 
 [[package]]
 name = "openai"
-version = "1.55.3"
+version = "1.60.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
@@ -976,9 +974,9 @@ dependencies = [
     { name = "tqdm" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/1e/39/d4859d897da053b61b84403f67dbef1abd075e441cb354892ff14f98e2c7/openai-1.55.3.tar.gz", hash = "sha256:547e85b94535469f137a779d8770c8c5adebd507c2cc6340ca401a7c4d5d16f0", size = 314571 }
+sdist = { url = "https://files.pythonhosted.org/packages/08/ae/8d9706b8ff2363287b4a8807de2dd29cdbdad5424e9d05d345df724320f5/openai-1.60.2.tar.gz", hash = "sha256:a8f843e10f2855713007f491d96afb2694b11b5e02cb97c7d01a0be60bc5bb51", size = 348185 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/10/06/691ef3f0112ecf0d7420d0bf35b5d16cf81554141f4b4913a9831031013d/openai-1.55.3-py3-none-any.whl", hash = "sha256:2a235d0e1e312cd982f561b18c27692e253852f4e5fb6ccf08cb13540a9bdaa1", size = 389558 },
+    { url = "https://files.pythonhosted.org/packages/e5/5a/d5474ca67a547dde9b87b5bc8a8f90eadf29f523d410f2ba23d63c9b82ec/openai-1.60.2-py3-none-any.whl", hash = "sha256:993bd11b96900b9098179c728026f016b4982ded7ee30dfcf4555eab1171fff9", size = 456107 },
 ]
 
 [[package]]
@@ -1005,11 +1003,11 @@ requires-dist = [
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
     { name = "events", editable = "../events" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "pillow", specifier = ">=11.0.0" },
     { name = "python-liquid", specifier = ">=1.12.1" },
     { name = "semantic-workbench-assistant", editable = "../semantic-workbench-assistant" },
-    { name = "tiktoken", specifier = ">=0.7.0" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
 ]
 
 [package.metadata.requires-dev]
@@ -1117,7 +1115,7 @@ name = "portalocker"
 version = "2.10.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "pywin32", marker = "platform_system == 'Windows'" },
+    { name = "pywin32", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/ed/d3/c6c64067759e87af98cc668c1cc75171347d0f1577fab7ca3749134e3cd4/portalocker-2.10.1.tar.gz", hash = "sha256:ef1bf844e878ab08aee7e40184156e1151f228f103aa5c6bd0724cc330960f8f", size = 40891 }
 wheels = [
@@ -1666,7 +1664,7 @@ name = "tqdm"
 version = "4.67.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/a8/4b/29b4ef32e036bb34e4ab51796dd745cdba7ed47ad142a9f4a1eb8e0c744d/tqdm-4.67.1.tar.gz", hash = "sha256:f8aef9c52c08c13a65f30ea34f4e5aac3fd1a34959879d7e59e63027286627f2", size = 169737 }
 wheels = [
diff --git a/libraries/python/assistant-extensions/assistant_extensions/ai_clients/model.py b/libraries/python/assistant-extensions/assistant_extensions/ai_clients/model.py
index e212af8b..2ae48433 100644
--- a/libraries/python/assistant-extensions/assistant_extensions/ai_clients/model.py
+++ b/libraries/python/assistant-extensions/assistant_extensions/ai_clients/model.py
@@ -19,7 +19,7 @@ class CompletionMessageTextContent:
 
 @dataclass
 class CompletionMessage:
-    role: Literal["assistant", "user", "system"]
+    role: Literal["assistant", "user", "system", "developer"]
     content: str | list[CompletionMessageImageContent | CompletionMessageTextContent]
 
 
diff --git a/libraries/python/assistant-extensions/pyproject.toml b/libraries/python/assistant-extensions/pyproject.toml
index 961e192a..196a9332 100644
--- a/libraries/python/assistant-extensions/pyproject.toml
+++ b/libraries/python/assistant-extensions/pyproject.toml
@@ -13,7 +13,7 @@ dependencies = [
     "anthropic>=0.40.0",
     "anthropic-client>=0.1.0",
     "assistant-drive>=0.1.0",
-    "openai>=1.51.2",
+    "openai>=1.60.2",
     "openai-client>=0.1.0",
     "requests-sse>=0.3.2",
     "semantic-workbench-assistant>=0.1.0",
diff --git a/libraries/python/assistant-extensions/uv.lock b/libraries/python/assistant-extensions/uv.lock
index 0b3913a1..dfed13fc 100644
--- a/libraries/python/assistant-extensions/uv.lock
+++ b/libraries/python/assistant-extensions/uv.lock
@@ -230,7 +230,7 @@ requires-dist = [
     { name = "assistant-drive", editable = "../assistant-drive" },
     { name = "assistant-drive", marker = "extra == 'attachments'", editable = "../assistant-drive" },
     { name = "docx2txt", marker = "extra == 'attachments'", specifier = ">=0.8" },
-    { name = "openai", specifier = ">=1.51.2" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "openai-client", editable = "../openai-client" },
     { name = "pdfplumber", marker = "extra == 'attachments'", specifier = ">=0.11.2" },
     { name = "requests-sse", specifier = ">=0.3.2" },
@@ -423,7 +423,7 @@ name = "click"
 version = "8.1.7"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/96/d3/f04c7bfcf5c1862a2a5b845c6b2b360488cf47af55dfa79c98f6a6bf98b5/click-8.1.7.tar.gz", hash = "sha256:ca9853ad459e787e2192211578cc907e7594e294c7ccc834310722b41b9ca6de", size = 336121 }
 wheels = [
@@ -956,7 +956,7 @@ wheels = [
 
 [[package]]
 name = "openai"
-version = "1.51.2"
+version = "1.60.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
@@ -968,9 +968,9 @@ dependencies = [
     { name = "tqdm" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/95/64/9a5279138b5ea6c2f0e5443d5d93b4510cb87fa6fe7be0c92b837087124e/openai-1.51.2.tar.gz", hash = "sha256:c6a51fac62a1ca9df85a522e462918f6bb6bc51a8897032217e453a0730123a6", size = 307755 }
+sdist = { url = "https://files.pythonhosted.org/packages/08/ae/8d9706b8ff2363287b4a8807de2dd29cdbdad5424e9d05d345df724320f5/openai-1.60.2.tar.gz", hash = "sha256:a8f843e10f2855713007f491d96afb2694b11b5e02cb97c7d01a0be60bc5bb51", size = 348185 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/3d/49/72198d0941b3a0264b6d13033823025c01c497f1cbfd83db310392c49c0e/openai-1.51.2-py3-none-any.whl", hash = "sha256:5c5954711cba931423e471c37ff22ae0fd3892be9b083eee36459865fbbb83fa", size = 383687 },
+    { url = "https://files.pythonhosted.org/packages/e5/5a/d5474ca67a547dde9b87b5bc8a8f90eadf29f523d410f2ba23d63c9b82ec/openai-1.60.2-py3-none-any.whl", hash = "sha256:993bd11b96900b9098179c728026f016b4982ded7ee30dfcf4555eab1171fff9", size = 456107 },
 ]
 
 [[package]]
@@ -997,11 +997,11 @@ requires-dist = [
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
     { name = "events", editable = "../events" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "pillow", specifier = ">=11.0.0" },
     { name = "python-liquid", specifier = ">=1.12.1" },
     { name = "semantic-workbench-assistant", editable = "../semantic-workbench-assistant" },
-    { name = "tiktoken", specifier = ">=0.7.0" },
+    { name = "tiktoken", specifier = ">=0.8.0" },
 ]
 
 [package.metadata.requires-dev]
@@ -1109,7 +1109,7 @@ name = "portalocker"
 version = "2.10.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "pywin32", marker = "platform_system == 'Windows'" },
+    { name = "pywin32", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/ed/d3/c6c64067759e87af98cc668c1cc75171347d0f1577fab7ca3749134e3cd4/portalocker-2.10.1.tar.gz", hash = "sha256:ef1bf844e878ab08aee7e40184156e1151f228f103aa5c6bd0724cc330960f8f", size = 40891 }
 wheels = [
@@ -1664,7 +1664,7 @@ name = "tqdm"
 version = "4.66.5"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/58/83/6ba9844a41128c62e810fddddd72473201f3eacde02046066142a2d96cc5/tqdm-4.66.5.tar.gz", hash = "sha256:e1020aef2e5096702d8a025ac7d16b1577279c9d63f8375b63083e9a5f0fcbad", size = 169504 }
 wheels = [
diff --git a/libraries/python/content-safety/pyproject.toml b/libraries/python/content-safety/pyproject.toml
index 8e479626..ef246ad6 100644
--- a/libraries/python/content-safety/pyproject.toml
+++ b/libraries/python/content-safety/pyproject.toml
@@ -9,7 +9,7 @@ dependencies = [
     "azure-ai-contentsafety>=1.0.0",
     "azure-core[aio]>=1.30.0",
     "azure-identity>=1.17.1",
-    "openai>=1.3.9",
+    "openai>=1.60.2",
     "semantic-workbench-assistant>=0.1.0",
 ]
 
@@ -24,6 +24,4 @@ requires = ["hatchling"]
 build-backend = "hatchling.build"
 
 [dependency-groups]
-dev = [
-    "pyright>=1.1.389",
-]
+dev = ["pyright>=1.1.389"]
diff --git a/libraries/python/content-safety/uv.lock b/libraries/python/content-safety/uv.lock
index 7bac5934..6c0dd734 100644
--- a/libraries/python/content-safety/uv.lock
+++ b/libraries/python/content-safety/uv.lock
@@ -285,7 +285,7 @@ name = "click"
 version = "8.1.7"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/96/d3/f04c7bfcf5c1862a2a5b845c6b2b360488cf47af55dfa79c98f6a6bf98b5/click-8.1.7.tar.gz", hash = "sha256:ca9853ad459e787e2192211578cc907e7594e294c7ccc834310722b41b9ca6de", size = 336121 }
 wheels = [
@@ -323,7 +323,7 @@ requires-dist = [
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
-    { name = "openai", specifier = ">=1.3.9" },
+    { name = "openai", specifier = ">=1.60.2" },
     { name = "semantic-workbench-assistant", editable = "../semantic-workbench-assistant" },
 ]
 
@@ -746,7 +746,7 @@ wheels = [
 
 [[package]]
 name = "openai"
-version = "1.51.0"
+version = "1.60.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
@@ -758,9 +758,9 @@ dependencies = [
     { name = "tqdm" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/28/af/cc59b1447f5a02bb1f25b9b0cd94b607aa2c969a81d9a244d4067f91f6fe/openai-1.51.0.tar.gz", hash = "sha256:8dc4f9d75ccdd5466fc8c99a952186eddceb9fd6ba694044773f3736a847149d", size = 306880 }
+sdist = { url = "https://files.pythonhosted.org/packages/08/ae/8d9706b8ff2363287b4a8807de2dd29cdbdad5424e9d05d345df724320f5/openai-1.60.2.tar.gz", hash = "sha256:a8f843e10f2855713007f491d96afb2694b11b5e02cb97c7d01a0be60bc5bb51", size = 348185 }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/c7/08/9f22356d4fbd273f734db1e6663b7ca6987943080567f5580471022e57ca/openai-1.51.0-py3-none-any.whl", hash = "sha256:d9affafb7e51e5a27dce78589d4964ce4d6f6d560307265933a94b2e3f3c5d2c", size = 383533 },
+    { url = "https://files.pythonhosted.org/packages/e5/5a/d5474ca67a547dde9b87b5bc8a8f90eadf29f523d410f2ba23d63c9b82ec/openai-1.60.2-py3-none-any.whl", hash = "sha256:993bd11b96900b9098179c728026f016b4982ded7ee30dfcf4555eab1171fff9", size = 456107 },
 ]
 
 [[package]]
@@ -768,7 +768,7 @@ name = "portalocker"
 version = "2.10.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "pywin32", marker = "platform_system == 'Windows'" },
+    { name = "pywin32", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/ed/d3/c6c64067759e87af98cc668c1cc75171347d0f1577fab7ca3749134e3cd4/portalocker-2.10.1.tar.gz", hash = "sha256:ef1bf844e878ab08aee7e40184156e1151f228f103aa5c6bd0724cc330960f8f", size = 40891 }
 wheels = [
@@ -1095,7 +1095,7 @@ name = "tqdm"
 version = "4.66.5"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/58/83/6ba9844a41128c62e810fddddd72473201f3eacde02046066142a2d96cc5/tqdm-4.66.5.tar.gz", hash = "sha256:e1020aef2e5096702d8a025ac7d16b1577279c9d63f8375b63083e9a5f0fcbad", size = 169504 }
 wheels = [
diff --git a/libraries/python/openai-client/openai_client/client.py b/libraries/python/openai-client/openai_client/client.py
index c8f7645e..4714dfa5 100644
--- a/libraries/python/openai-client/openai_client/client.py
+++ b/libraries/python/openai-client/openai_client/client.py
@@ -11,7 +11,7 @@
 )
 
 
-def create_client(service_config: ServiceConfig, *, api_version: str = "2024-08-01-preview") -> AsyncOpenAI:
+def create_client(service_config: ServiceConfig, *, api_version: str = "2024-12-01-preview") -> AsyncOpenAI:
     """
     Creates an AsyncOpenAI client based on the provided service configuration.
     """
diff --git a/libraries/python/openai-client/openai_client/config.py b/libraries/python/openai-client/openai_client/config.py
index be21088d..9b4a1de7 100644
--- a/libraries/python/openai-client/openai_client/config.py
+++ b/libraries/python/openai-client/openai_client/config.py
@@ -171,11 +171,23 @@ class OpenAIRequestConfig(RequestConfigBaseModel):
     is_reasoning_model: Annotated[
         bool,
         Field(
-            title="Is Reasoning Model (o1-preview, o1-mini, etc)",
-            description="Experimental: enable support for reasoning models such as o1-preview, o1-mini, etc.",
+            title="Is Reasoning Model (o1, o1-preview, o1-mini, etc)",
+            description="Experimental: enable support for reasoning models such as o1, o1-preview, o1-mini, etc.",
         ),
     ] = False
 
+    reasoning_effort: Annotated[
+        Literal["low", "medium", "high"],
+        Field(
+            title="Reasoning Effort",
+            description=(
+                "Constrains effort on reasoning for reasoning models. Currently supported values are low, medium, and"
+                " high. Reducing reasoning effort can result in faster responses and fewer tokens used on reasoning in"
+                " a response."
+            ),
+        ),
+    ] = "medium"
+
 
 """
 Open AI client service configuration, allowing AzureOpenAIServiceConfig or OpenAIServiceConfig.
diff --git a/libraries/python/openai-client/openai_client/messages.py b/libraries/python/openai-client/openai_client/messages.py
index 34628722..64fbeed8 100644
--- a/libraries/python/openai-client/openai_client/messages.py
+++ b/libraries/python/openai-client/openai_client/messages.py
@@ -8,6 +8,7 @@
 from liquid import Template
 from openai.types.chat import (
     ChatCompletionAssistantMessageParam,
+    ChatCompletionDeveloperMessageParam,
     ChatCompletionMessageParam,
     ChatCompletionMessageToolCallParam,
     ChatCompletionSystemMessageParam,
@@ -17,9 +18,10 @@
 
 def truncate_messages_for_logging(
     messages: list[ChatCompletionMessageParam],
-    truncate_messages_for_roles: set[Literal["user", "system", "assistant", "tool", "function"]] = {
+    truncate_messages_for_roles: set[Literal["user", "system", "developer", "assistant", "tool", "function"]] = {
         "user",
         "system",
+        "developer",
         "assistant",
     },
     maximum_content_length: int = 500,
@@ -121,6 +123,14 @@ def create_system_message(
     return {"role": "system", "content": content}
 
 
+def create_developer_message(
+    content: str, var: dict[str, Any] | None = None, formatter: MessageFormatter = format_with_liquid
+) -> ChatCompletionDeveloperMessageParam:
+    if var:
+        content = formatter(content, var)
+    return {"role": "developer", "content": content}
+
+
 def create_user_message(
     content: str | list[CompletionMessageImageContent | CompletionMessageTextContent],
     var: dict[str, Any] | None = None,
@@ -173,6 +183,14 @@ def convert_from_completion_messages(
             )
             continue
 
+        if message.role == "developer" and isinstance(message.content, str):
+            messages.append(
+                create_developer_message(
+                    content=message.content,
+                )
+            )
+            continue
+
         if message.role == "assistant" and isinstance(message.content, str):
             messages.append(
                 create_assistant_message(
diff --git a/libraries/python/openai-client/openai_client/tokens.py b/libraries/python/openai-client/openai_client/tokens.py
index 46ca842d..3c10fcb9 100644
--- a/libraries/python/openai-client/openai_client/tokens.py
+++ b/libraries/python/openai-client/openai_client/tokens.py
@@ -23,12 +23,7 @@ def num_tokens_from_message(message: ChatCompletionMessageParam, model: str) ->
     Reference: https://cookbook.openai.com/examples/how_to_count_tokens_with_tiktoken#6-counting-tokens-for-chat-completions-api-calls
     """
 
-    try:
-        encoding = tiktoken.encoding_for_model(model)
-    except KeyError:
-        logger.warning("model %s not found. Using cl100k_base encoding.", model)
-        encoding = tiktoken.get_encoding("cl100k_base")
-
+    # First, set the default number of tokens per message and per name and convert generic model names to specific ones
     if model in {
         "gpt-3.5-turbo-0125",
         "gpt-4-0314",
@@ -38,8 +33,7 @@ def num_tokens_from_message(message: ChatCompletionMessageParam, model: str) ->
         "gpt-4o-mini-2024-07-18",
         "gpt-4o-2024-08-06",
         # TODO: determine correct handling of reasoning models
-        "o1-preview",
-        "o1-mini",
+        "o1-2024-12-17",
     }:
         tokens_per_message = 3
         tokens_per_name = 1
@@ -55,9 +49,19 @@ def num_tokens_from_message(message: ChatCompletionMessageParam, model: str) ->
     elif "gpt-4" in model:
         logger.debug("gpt-4 may update over time. Returning num tokens assuming gpt-4-0613.")
         return num_tokens_from_message(message, model="gpt-4-0613")
+    elif model.startswith("o1"):
+        logger.debug("o1-* may update over time. Returning num tokens assuming o1-2024-12-17.")
+        return num_tokens_from_message(message, model="o1-2024-12-17")
     else:
         raise NotImplementedError(f"num_tokens_from_messages() is not implemented for model {model}.")
 
+    # Then, calculate the number of tokens for the message now that we have the correct specific model name
+    try:
+        encoding = tiktoken.encoding_for_model(model)
+    except KeyError:
+        logger.warning("model %s not found. Using cl100k_base encoding.", model)
+        encoding = tiktoken.get_encoding("cl100k_base")
+
     num_tokens = tokens_per_message
     for key, value in message.items():
         if isinstance(value, list):
diff --git a/libraries/python/openai-client/pyproject.toml b/libraries/python/openai-client/pyproject.toml
index f832186b..9d791218 100644
--- a/libraries/python/openai-client/pyproject.toml
+++ b/libraries/python/openai-client/pyproject.toml
@@ -11,11 +11,11 @@ dependencies = [
     "azure-core[aio]>=1.30.0",
     "azure-identity>=1.17.1",
     "events>=0.1.0",
-    "openai>=1.3.9",
+    "openai>=1.60.2",
     "pillow>=11.0.0",
     "python-liquid>=1.12.1",
     "semantic-workbench-assistant>=0.1.0",
-    "tiktoken>=0.7.0",
+    "tiktoken>=0.8.0",
 ]
 
 [dependency-groups]
diff --git a/libraries/python/openai-client/uv.lock b/libraries/python/openai-client/uv.lock
index e27ff36c..838b96ed 100644
--- a/libraries/python/openai-client/uv.lock
+++ b/libraries/python/openai-client/uv.lock
@@ -1,22 +1,18 @@
 version = 1
 requires-python = ">=3.11"
-resolution-markers = [
-    "python_full_version < '3.13'",
-    "python_full_version >= '3.13'",
-]
 
 [[package]]
 name = "aiohappyeyeballs"
-version = "2.4.3"
+version = "2.4.4"
 source = { registry = "https://pypi.org/simple" }
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+sdist = { url = "https://files.pythonhosted.org/packages/7f/55/e4373e888fdacb15563ef6fa9fa8c8252476ea071e96fb46defac9f18bf2/aiohappyeyeballs-2.4.4.tar.gz", hash = "sha256:5fdd7d87889c63183afc18ce9271f9b0a7d32c2303e394468dd45d514a757745", size = 21977 }
 wheels = [
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+    { url = "https://files.pythonhosted.org/packages/b9/74/fbb6559de3607b3300b9be3cc64e97548d55678e44623db17820dbd20002/aiohappyeyeballs-2.4.4-py3-none-any.whl", hash = "sha256:a980909d50efcd44795c4afeca523296716d50cd756ddca6af8c65b996e27de8", size = 14756 },
 ]
 
 [[package]]
 name = "aiohttp"
-version = "3.10.9"
+version = "3.11.11"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "aiohappyeyeballs" },
@@ -24,67 +20,68 @@ dependencies = [
     { name = "attrs" },
     { name = "frozenlist" },
     { name = "multidict" },
+    { name = "propcache" },
     { name = "yarl" },
 ]
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diff --git a/libraries/python/skills/notebooks/uv.lock b/libraries/python/skills/notebooks/uv.lock
index c46a20d2..2a042858 100644
--- a/libraries/python/skills/notebooks/uv.lock
+++ b/libraries/python/skills/notebooks/uv.lock
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diff --git a/libraries/python/skills/skill-library/pyproject.toml b/libraries/python/skills/skill-library/pyproject.toml
index 1cde726d..9aee5821 100644
--- a/libraries/python/skills/skill-library/pyproject.toml
+++ b/libraries/python/skills/skill-library/pyproject.toml
@@ -17,7 +17,7 @@ dependencies = [
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index 3faf256c..361eaf7f 100644
--- a/libraries/python/skills/skill-library/uv.lock
+++ b/libraries/python/skills/skill-library/uv.lock
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-    { name = "tiktoken", specifier = ">=0.7.0" },
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diff --git a/libraries/python/skills/skills/common-skill/uv.lock b/libraries/python/skills/skills/common-skill/uv.lock
index 3c06404b..8f662e0e 100644
--- a/libraries/python/skills/skills/common-skill/uv.lock
+++ b/libraries/python/skills/skills/common-skill/uv.lock
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@@ -1198,7 +1198,7 @@ wheels = [
 
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index 0122bc25..0e5c0b54 100644
--- a/libraries/python/skills/skills/document-skill/uv.lock
+++ b/libraries/python/skills/skills/document-skill/uv.lock
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diff --git a/libraries/python/skills/skills/posix-skill/uv.lock b/libraries/python/skills/skills/posix-skill/uv.lock
index fba38e4c..b06494b2 100644
--- a/libraries/python/skills/skills/posix-skill/uv.lock
+++ b/libraries/python/skills/skills/posix-skill/uv.lock
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 dependencies = [
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index feb0a080..31f0b529 100644
--- a/libraries/python/skills/skills/prospector-skill/uv.lock
+++ b/libraries/python/skills/skills/prospector-skill/uv.lock
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index db23ae7a..9958fcc5 100644
--- a/libraries/python/skills/skills/skill-template/uv.lock
+++ b/libraries/python/skills/skills/skill-template/uv.lock
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 [[package]]
@@ -1628,7 +1632,7 @@ name = "tqdm"
 version = "4.66.5"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "colorama", marker = "platform_system == 'Windows'" },
+    { name = "colorama", marker = "sys_platform == 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/58/83/6ba9844a41128c62e810fddddd72473201f3eacde02046066142a2d96cc5/tqdm-4.66.5.tar.gz", hash = "sha256:e1020aef2e5096702d8a025ac7d16b1577279c9d63f8375b63083e9a5f0fcbad", size = 169504 }
 wheels = [
diff --git a/workspaces-app/.vscode/settings.json b/workspaces-app/.vscode/settings.json
new file mode 100644
index 00000000..b18e8357
--- /dev/null
+++ b/workspaces-app/.vscode/settings.json
@@ -0,0 +1,3 @@
+{
+  "cSpell.words": ["fluentui"]
+}
diff --git a/workspaces-app/README.md b/workspaces-app/README.md
index 90858f69..a21c0b80 100644
--- a/workspaces-app/README.md
+++ b/workspaces-app/README.md
@@ -1,21 +1,21 @@
 # High-Level Plan for AI Assistant Chat Application
 
-This project will create an AI assistant chat experience using a React and TypeScript frontend built with Vite and RTK Query, interacting with a backend Python REST service.
+This project creates an AI assistant chat experience using a React and TypeScript frontend built with Vite and RTK Query, interacting with a backend Python REST service. We are using Fluent UI React v9 for the UI components to enhance the app's appearance and user experience.
 
-**Plan:**
+**Development Plan:**
 
 1. **Initialize Project**
    - Create a new Vite project with React and TypeScript.
    - Set up project structure for components and services.
 
-2. **Set Up State Management**
+2. **Set Up State Management and Styling**
    - Integrate Redux Toolkit and RTK Query for efficient state management and data fetching.
 
-3. **Develop Chat Interface**
-   - Create user interface components for the chat experience.
-   - Implement styling and responsiveness.
+3. **Develop Chat Interface with Fluent UI React**
+   - Use Fluent UI React components to create user interface elements for the chat experience.
+   - Implement styling and responsiveness using Fluent UI's design system.
 
-4. **Connect to Backend Python REST Service**
+4. **Connect to Backend Python REST Service using RTK Query**
    - Configure RTK Query API slices to communicate with the Python REST backend.
    - Ensure secure communication and error handling.
 
@@ -27,10 +27,68 @@ This project will create an AI assistant chat experience using a React and TypeS
    - Write unit and integration tests.
    - Prepare the application for deployment and set up CI/CD pipelines.
 
-7. **Documentation**
-   - Document the codebase and provide setup instructions.
-   - Update the README with usage guidelines and contribution instructions.
+7. **Final Documentation and README Update**
+   - Document the codebase and provide setup instructions. Include details on using pnpm for package management and introducing Fluent UI React components into the project.
+   - Update the README with usage guidelines, including commands for package installation and example code for integrating Fluent UI.
+ - Encourage contributions by providing guidelines for submitting improvements or new features.
 
 ---
 
+## Folder Structure
+
+The following is the proposed folder structure for the AI assistant chat application:
+
+```
+/workspaces-app
+|-- /public
+|   |-- index.html                # HTML entry point
+|   |-- favicon.ico               # Application icon
+|
+|-- /src
+|   |-- /assets                  # Static assets (images, fonts, etc.)
+|   |-- /components              # Reusable React components
+|   |   |-- ChatWindow.tsx       # Main chat interface component
+|   |   |-- MessageList.tsx      # Component to display chat messages
+|   |   `-- MessageInput.tsx     # Input component for sending messages
+|   |
+|   |-- /contexts                # Context providers for global state
+|   |   `-- ThemeContext.tsx     # Example for theming
+|   |
+|   |-- /features                # RTK slices and features
+|   |   |-- chatSlice.ts         # RTK slice for managing chat state
+|   |
+|   |-- /hooks                   # Custom React hooks
+|   |   `-- useChatEvents.ts     # Hook for handling SSE
+|   |
+|   |-- /services                # API services and configurations
+|   |   |-- api.ts               # RTK Query API setup
+|   |   `-- sseClient.ts         # SSE client handling
+|   |
+|   |-- /styles                  # Styling files
+|   |   `-- main.css             # Custom global styles
+|   |
+|   |-- /utils                   # Utility functions and helpers
+|   |   `-- helpers.ts           # General purpose helper functions
+|   |
+|   `-- App.tsx                  # Main application component
+|   `-- index.tsx                # Application entry point
+|
+|-- package.json                 # Package manifest
+|-- tsconfig.json                # TypeScript configuration
+|-- README.md                    # Project documentation
+```
+
+### Highlights of the Structure:
+
+- **`/public`**: Contains static files like `index.html` and others that do not need to be processed by the build tool.
+- **`/src/components`**: Dedicated to the individual UI components of your application.
+- **`/src/features`**: Contains Redux slices and features for organizing state management.
+- **`/src/hooks`**: A place for custom hooks like those handling SSE interactions.
+- **`/src/services`**: Service-related code such as API configuration and SSE client handling.
+- **`/src/styles`**: Centralized styling files, which could use CSS, SCSS, or CSS-in-JS solutions.
+- **`/src/utils`**: Utility functions and helpers shared across the application.
+
+This structure provides separation of concerns and a clear organization that should make future modifications and additions easier.
+
+
 This README outlines the high-level plan to guide the development of the AI assistant chat application.
\ No newline at end of file
diff --git a/workspaces-app/package.json b/workspaces-app/package.json
index fe417d60..3b49c64e 100644
--- a/workspaces-app/package.json
+++ b/workspaces-app/package.json
@@ -8,14 +8,18 @@
     "preview": "vite preview"
   },
   "dependencies": {
-    "react": "^17.0.2",
-    "react-dom": "^17.0.2",
-    "@reduxjs/toolkit": "^1.7.1",
-    "react-redux": "^7.2.6"
+    "@fluentui/react-components": "^9.58.1",
+    "@reduxjs/toolkit": "^2.5.1",
+    "react": "^18.3.1",
+    "react-dom": "^18.3.1",
+    "react-redux": "^9.2.0",
+    "scheduler": "0.23.0"
   },
   "devDependencies": {
-    "typescript": "^4.5.4",
-    "vite": "^2.6.14",
-    "@vitejs/plugin-react-refresh": "^1.3.6"
+    "@types/react": "^19.0.8",
+    "@types/react-dom": "^19.0.3",
+    "@vitejs/plugin-react-refresh": "^1.3.6",
+    "typescript": "^5.7.3",
+    "vite": "^6.0.11"
   }
 }
\ No newline at end of file
diff --git a/workspaces-app/pnpm-lock.yaml b/workspaces-app/pnpm-lock.yaml
new file mode 100644
index 00000000..83e6cc2b
--- /dev/null
+++ b/workspaces-app/pnpm-lock.yaml
@@ -0,0 +1,2870 @@
+lockfileVersion: '9.0'
+
+settings:
+  autoInstallPeers: true
+  excludeLinksFromLockfile: false
+
+importers:
+
+  .:
+    dependencies:
+      '@fluentui/react-components':
+        specifier: ^9.58.1
+        version: 9.58.1(@types/react-dom@19.0.3(@types/react@19.0.8))(@types/react@19.0.8)(react-dom@18.3.1(react@18.3.1))(react@18.3.1)(scheduler@0.23.0)
+      '@reduxjs/toolkit':
+        specifier: ^2.5.1
+        version: 2.5.1(react-redux@9.2.0(@types/react@19.0.8)(react@18.3.1)(redux@5.0.1))(react@18.3.1)
+      react:
+        specifier: ^18.3.1
+        version: 18.3.1
+      react-dom:
+        specifier: ^18.3.1
+        version: 18.3.1(react@18.3.1)
+      react-redux:
+        specifier: ^9.2.0
+        version: 9.2.0(@types/react@19.0.8)(react@18.3.1)(redux@5.0.1)
+      scheduler:
+        specifier: 0.23.0
+        version: 0.23.0
+    devDependencies:
+      '@types/react':
+        specifier: ^19.0.8
+        version: 19.0.8
+      '@types/react-dom':
+        specifier: ^19.0.3
+        version: 19.0.3(@types/react@19.0.8)
+      '@vitejs/plugin-react-refresh':
+        specifier: ^1.3.6
+        version: 1.3.6
+      typescript:
+        specifier: ^5.7.3
+        version: 5.7.3
+      vite:
+        specifier: ^6.0.11
+        version: 6.0.11
+
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+
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+      embla-carousel-fade: 8.5.2(embla-carousel@8.5.2)
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+    transitivePeerDependencies:
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+      - scheduler
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+      escalade: 3.2.0
+      picocolors: 1.1.1
+
+  use-disposable@1.0.4(@types/react-dom@19.0.3(@types/react@19.0.8))(@types/react@19.0.8)(react-dom@18.3.1(react@18.3.1))(react@18.3.1):
+    dependencies:
+      '@types/react': 19.0.8
+      '@types/react-dom': 19.0.3(@types/react@19.0.8)
+      react: 18.3.1
+      react-dom: 18.3.1(react@18.3.1)
+
+  use-sync-external-store@1.4.0(react@18.3.1):
+    dependencies:
+      react: 18.3.1
+
+  vite@6.0.11:
+    dependencies:
+      esbuild: 0.24.2
+      postcss: 8.5.1
+      rollup: 4.32.0
+    optionalDependencies:
+      fsevents: 2.3.3
+
+  yallist@3.1.1: {}
diff --git a/workspaces-app/src/App.tsx b/workspaces-app/src/App.tsx
new file mode 100644
index 00000000..18e01dc0
--- /dev/null
+++ b/workspaces-app/src/App.tsx
@@ -0,0 +1,14 @@
+import React from "react";
+
+// Define the App component
+const App: React.FC = () => {
+  return (
+    <div>
+      <h1>Welcome to the AI Assistant Chat Application</h1>
+      <p>This is a basic setup. More features will be added soon!</p>
+    </div>
+  );
+};
+
+// Export the component as the default export
+export default App;
\ No newline at end of file
diff --git a/workspaces-app/src/index.tsx b/workspaces-app/src/index.tsx
new file mode 100644
index 00000000..3dbf5b58
--- /dev/null
+++ b/workspaces-app/src/index.tsx
@@ -0,0 +1,21 @@
+// Importing necessary dependencies
+import React from "react";
+import ReactDOM from "react-dom/client";
+import App from "./App";
+
+// Creating a root element to render the app
+const root = document.getElementById("root");
+
+if (root) {
+  // Creating a root container for React 18
+  const reactRoot = ReactDOM.createRoot(root);
+
+  // Rendering the App component
+  reactRoot.render(
+    <React.StrictMode>
+      <App />
+    </React.StrictMode>
+  );
+} else {
+  console.error("Failed to find the root element. Make sure there is an element with id 'root' in your HTML.");
+}
\ No newline at end of file