diff --git a/assistants/explorer-assistant/uv.lock b/assistants/explorer-assistant/uv.lock
index 6e3bec8d..f7a63665 100644
--- a/assistants/explorer-assistant/uv.lock
+++ b/assistants/explorer-assistant/uv.lock
@@ -1100,7 +1100,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../libraries/python/openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -1114,7 +1114,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../libraries/python/assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../libraries/python/assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
diff --git a/assistants/guided-conversation-assistant/uv.lock b/assistants/guided-conversation-assistant/uv.lock
index 7cb2ed88..cbab48e5 100644
--- a/assistants/guided-conversation-assistant/uv.lock
+++ b/assistants/guided-conversation-assistant/uv.lock
@@ -252,6 +252,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
     { name = "anthropic", specifier = ">=0.40.0" },
@@ -1229,7 +1236,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../libraries/python/openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -1243,7 +1250,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../libraries/python/assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../libraries/python/assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
diff --git a/assistants/prospector-assistant/uv.lock b/assistants/prospector-assistant/uv.lock
index 711b1286..bdfbd9dc 100644
--- a/assistants/prospector-assistant/uv.lock
+++ b/assistants/prospector-assistant/uv.lock
@@ -1259,7 +1259,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../libraries/python/openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -1273,7 +1273,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../libraries/python/assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../libraries/python/assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
@@ -2183,6 +2183,7 @@ version = "0.1.0"
 source = { editable = "../../libraries/python/skills/skill-library" }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -2197,6 +2198,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../libraries/python/assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../libraries/python/assistant-extensions" },
     { name = "context", editable = "../../libraries/python/context" },
     { name = "events", editable = "../../libraries/python/events" },
     { name = "openai", specifier = ">=1.16.1" },
diff --git a/assistants/skill-assistant/uv.lock b/assistants/skill-assistant/uv.lock
index d51031bc..b4c3f64f 100644
--- a/assistants/skill-assistant/uv.lock
+++ b/assistants/skill-assistant/uv.lock
@@ -259,6 +259,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
     { name = "anthropic", specifier = ">=0.40.0" },
@@ -622,6 +629,12 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/68/1b/e0a87d256e40e8c888847551b20a017a6b98139178505dc7ffb96f04e954/dnspython-2.7.0-py3-none-any.whl", hash = "sha256:b4c34b7d10b51bcc3a5071e7b8dee77939f1e878477eeecc965e9835f63c6c86", size = 313632 },
 ]
 
+[[package]]
+name = "docx2txt"
+version = "0.8"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/7d/7d/60ee3f2b16d9bfdfa72e8599470a2c1a5b759cb113c6fe1006be28359327/docx2txt-0.8.tar.gz", hash = "sha256:2c06d98d7cfe2d3947e5760a57d924e3ff07745b379c8737723922e7009236e5", size = 2814 }
+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -697,6 +710,7 @@ version = "0.1.0"
 source = { editable = "../../libraries/python/skills/skills/form-filler-skill" }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "datamodel-code-generator" },
     { name = "events" },
@@ -707,6 +721,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../libraries/python/assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../libraries/python/assistant-extensions" },
     { name = "context", editable = "../../libraries/python/context" },
     { name = "datamodel-code-generator", specifier = ">=0.26.3" },
     { name = "events", editable = "../../libraries/python/events" },
@@ -1146,7 +1161,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../libraries/python/openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -1160,7 +1175,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../libraries/python/assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../libraries/python/assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
@@ -1196,6 +1211,33 @@ wheels = [
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 ]
 
+[[package]]
+name = "pdfminer-six"
+version = "20231228"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "charset-normalizer" },
+    { name = "cryptography" },
+]
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+]
+
+[[package]]
+name = "pdfplumber"
+version = "0.11.4"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "pdfminer-six" },
+    { name = "pillow" },
+    { name = "pypdfium2" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/ca/f0/457bda3629dfa5b01c645519fe30230e1739751f6645e23fca2dabf6c2e5/pdfplumber-0.11.4.tar.gz", hash = "sha256:147b55cde2351fcb9523b46b09cc771eea3602faecfb60d463c6bf951694fbe8", size = 113305 }
+wheels = [
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+]
+
 [[package]]
 name = "pillow"
 version = "11.0.0"
@@ -1456,6 +1498,26 @@ crypto = [
     { name = "cryptography" },
 ]
 
+[[package]]
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+]
+
 [[package]]
 name = "pyright"
 version = "1.1.389"
@@ -1744,6 +1806,7 @@ version = "0.1.0"
 source = { editable = "../../libraries/python/skills/skill-library" }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -1758,6 +1821,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../libraries/python/assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../libraries/python/assistant-extensions" },
     { name = "context", editable = "../../libraries/python/context" },
     { name = "events", editable = "../../libraries/python/events" },
     { name = "openai", specifier = ">=1.16.1" },
diff --git a/examples/python/python-02-simple-chatbot/uv.lock b/examples/python/python-02-simple-chatbot/uv.lock
index 93a6a0f4..95bce622 100644
--- a/examples/python/python-02-simple-chatbot/uv.lock
+++ b/examples/python/python-02-simple-chatbot/uv.lock
@@ -237,6 +237,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
     { name = "anthropic", specifier = ">=0.40.0" },
@@ -537,6 +544,12 @@ wheels = [
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 ]
 
+[[package]]
+name = "docx2txt"
+version = "0.8"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/7d/7d/60ee3f2b16d9bfdfa72e8599470a2c1a5b759cb113c6fe1006be28359327/docx2txt-0.8.tar.gz", hash = "sha256:2c06d98d7cfe2d3947e5760a57d924e3ff07745b379c8737723922e7009236e5", size = 2814 }
+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -942,7 +955,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../../libraries/python/openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -956,7 +969,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../../libraries/python/assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../libraries/python/assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
@@ -974,6 +987,33 @@ dev = [
     { name = "pytest", specifier = ">=8.3.3" },
 ]
 
+[[package]]
+name = "pdfminer-six"
+version = "20231228"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
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+]
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@@ -1141,6 +1181,26 @@ crypto = [
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diff --git a/examples/python/python-03-multimodel-chatbot/uv.lock b/examples/python/python-03-multimodel-chatbot/uv.lock
index 403853a3..f080f307 100644
--- a/examples/python/python-03-multimodel-chatbot/uv.lock
+++ b/examples/python/python-03-multimodel-chatbot/uv.lock
@@ -241,6 +241,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
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+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -1126,7 +1139,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../../libraries/python/openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -1140,7 +1153,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../../libraries/python/assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../libraries/python/assistant-extensions" },
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     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
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@@ -1158,6 +1171,33 @@ dev = [
     { name = "pytest", specifier = ">=8.3.3" },
 ]
 
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diff --git a/libraries/python/anthropic-client/uv.lock b/libraries/python/anthropic-client/uv.lock
index 1b1f1a39..3559fda8 100644
--- a/libraries/python/anthropic-client/uv.lock
+++ b/libraries/python/anthropic-client/uv.lock
@@ -212,6 +212,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
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 ]
 
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+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -973,7 +986,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -987,7 +1000,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
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diff --git a/libraries/python/assistant-extensions/uv.lock b/libraries/python/assistant-extensions/uv.lock
index 80b5cb3b..0b3913a1 100644
--- a/libraries/python/assistant-extensions/uv.lock
+++ b/libraries/python/assistant-extensions/uv.lock
@@ -978,7 +978,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -992,7 +992,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "." },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "." },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
     { name = "azure-identity", specifier = ">=1.17.1" },
diff --git a/libraries/python/openai-client/pyproject.toml b/libraries/python/openai-client/pyproject.toml
index 2382642b..d6d4e4e7 100644
--- a/libraries/python/openai-client/pyproject.toml
+++ b/libraries/python/openai-client/pyproject.toml
@@ -6,7 +6,7 @@ authors = [{ name = "Semantic Workbench Team" }]
 readme = "README.md"
 requires-python = ">=3.11"
 dependencies = [
-    "assistant-extensions>=0.1.0",
+    "assistant-extensions[attachments]>=0.1.0",
     "azure-ai-contentsafety>=1.0.0",
     "azure-core[aio]>=1.30.0",
     "azure-identity>=1.17.1",
diff --git a/libraries/python/openai-client/uv.lock b/libraries/python/openai-client/uv.lock
index daa26eea..e27ff36c 100644
--- a/libraries/python/openai-client/uv.lock
+++ b/libraries/python/openai-client/uv.lock
@@ -208,6 +208,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
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 ]
 
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+source = { registry = "https://pypi.org/simple" }
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+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -898,7 +911,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "." }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -918,7 +931,7 @@ dev = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
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 ]
 
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+source = { registry = "https://pypi.org/simple" }
+dependencies = [
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+    { name = "pillow" },
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 version = "11.0.0"
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diff --git a/libraries/python/skills/notebooks/uv.lock b/libraries/python/skills/notebooks/uv.lock
index c363e254..42c7c9d3 100644
--- a/libraries/python/skills/notebooks/uv.lock
+++ b/libraries/python/skills/notebooks/uv.lock
@@ -217,6 +217,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
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+version = "0.8"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/7d/7d/60ee3f2b16d9bfdfa72e8599470a2c1a5b759cb113c6fe1006be28359327/docx2txt-0.8.tar.gz", hash = "sha256:2c06d98d7cfe2d3947e5760a57d924e3ff07745b379c8737723922e7009236e5", size = 2814 }
+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -1082,7 +1095,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -1096,7 +1109,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
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+]
+
 [[package]]
 name = "pyright"
 version = "1.1.389"
@@ -1785,6 +1845,7 @@ version = "0.1.0"
 source = { editable = "../skill-library" }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -1799,6 +1860,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../assistant-extensions" },
     { name = "context", editable = "../../context" },
     { name = "events", editable = "../../events" },
     { name = "openai", specifier = ">=1.16.1" },
diff --git a/libraries/python/skills/skill-library/.vscode/settings.json b/libraries/python/skills/skill-library/.vscode/settings.json
index c287ac24..2c7a0316 100644
--- a/libraries/python/skills/skill-library/.vscode/settings.json
+++ b/libraries/python/skills/skill-library/.vscode/settings.json
@@ -59,6 +59,8 @@
     "openai",
     "pydantic",
     "pypdf",
+    "pyright",
+    "pytest",
     "runtimes",
     "subdrive",
     "tiktoken"
diff --git a/libraries/python/skills/skill-library/pyproject.toml b/libraries/python/skills/skill-library/pyproject.toml
index 62c7d593..6285dea9 100644
--- a/libraries/python/skills/skill-library/pyproject.toml
+++ b/libraries/python/skills/skill-library/pyproject.toml
@@ -7,6 +7,7 @@ readme = "README.md"
 requires-python = ">=3.11"
 dependencies = [
     "assistant-drive>=0.1.0",
+    "assistant-extensions[attachments]>=0.1.0",
     "context>=0.1.0",
     "events>=0.1.0",
     "openai-client>=0.1.0",
@@ -29,6 +30,7 @@ dev-dependencies = [
 
 [tool.uv.sources]
 assistant-drive = { path = "../../assistant-drive", editable = true }
+assistant-extensions = { path = "../../assistant-extensions", editable = true }
 context = { path = "../../context", editable = true }
 events = { path = "../../events", editable = true }
 openai-client = { path = "../../openai-client", editable = true }
diff --git a/libraries/python/skills/skill-library/uv.lock b/libraries/python/skills/skill-library/uv.lock
index 4fef6969..0efb0207 100644
--- a/libraries/python/skills/skill-library/uv.lock
+++ b/libraries/python/skills/skill-library/uv.lock
@@ -209,6 +209,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
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 requires-dist = [
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+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -965,7 +978,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -979,7 +992,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
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 ]
 
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+dependencies = [
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+    { name = "pillow" },
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+]
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+]
+
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 name = "pyright"
 version = "1.1.389"
@@ -1566,6 +1626,7 @@ version = "0.1.0"
 source = { editable = "." }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -1588,6 +1649,7 @@ dev = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../assistant-extensions" },
     { name = "context", editable = "../../context" },
     { name = "events", editable = "../../events" },
     { name = "openai", specifier = ">=1.16.1" },
diff --git a/libraries/python/skills/skills/document-skill/uv.lock b/libraries/python/skills/skills/document-skill/uv.lock
index 3ad630a2..e5351547 100644
--- a/libraries/python/skills/skills/document-skill/uv.lock
+++ b/libraries/python/skills/skills/document-skill/uv.lock
@@ -209,6 +209,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
     { name = "anthropic", specifier = ">=0.40.0" },
@@ -512,6 +519,12 @@ requires-dist = [
 [package.metadata.requires-dev]
 dev = [{ name = "pyright", specifier = ">=1.1.389" }]
 
+[[package]]
+name = "docx2txt"
+version = "0.8"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/7d/7d/60ee3f2b16d9bfdfa72e8599470a2c1a5b759cb113c6fe1006be28359327/docx2txt-0.8.tar.gz", hash = "sha256:2c06d98d7cfe2d3947e5760a57d924e3ff07745b379c8737723922e7009236e5", size = 2814 }
+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -956,7 +969,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../../openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -970,7 +983,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../../assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
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@@ -997,6 +1010,33 @@ wheels = [
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 ]
 
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+version = "0.11.4"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
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+    { name = "pillow" },
+    { name = "pypdfium2" },
+]
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 name = "pillow"
 version = "11.0.0"
@@ -1221,6 +1261,26 @@ crypto = [
     { name = "cryptography" },
 ]
 
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+]
+
 [[package]]
 name = "pyright"
 version = "1.1.389"
@@ -1506,6 +1566,7 @@ version = "0.1.0"
 source = { editable = "../../skill-library" }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -1520,6 +1581,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../../assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
     { name = "context", editable = "../../../context" },
     { name = "events", editable = "../../../events" },
     { name = "openai", specifier = ">=1.16.1" },
diff --git a/libraries/python/skills/skills/form-filler-skill/pyproject.toml b/libraries/python/skills/skills/form-filler-skill/pyproject.toml
index cd8dcb4c..7e77543a 100644
--- a/libraries/python/skills/skills/form-filler-skill/pyproject.toml
+++ b/libraries/python/skills/skills/form-filler-skill/pyproject.toml
@@ -7,6 +7,7 @@ readme = "README.md"
 requires-python = ">=3.11"
 dependencies = [
     "assistant-drive>=0.1.0",
+    "assistant-extensions[attachments]>=0.1.0",
     "context>=0.1.0",
     "datamodel-code-generator>=0.26.3",
     "events>=0.1.0",
@@ -28,6 +29,7 @@ package = true
 
 [tool.uv.sources]
 assistant-drive = { path = "../../../assistant-drive", editable = true }
+assistant-extensions = { path = "../../../assistant-extensions", editable = true }
 context = { path = "../../../context", editable = true }
 events = { path = "../../../events", editable = true }
 openai-client = { path = "../../../openai-client", editable = true }
diff --git a/libraries/python/skills/skills/form-filler-skill/uv.lock b/libraries/python/skills/skills/form-filler-skill/uv.lock
index ddf3c6f5..6b95558b 100644
--- a/libraries/python/skills/skills/form-filler-skill/uv.lock
+++ b/libraries/python/skills/skills/form-filler-skill/uv.lock
@@ -229,6 +229,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
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 ]
 
+[[package]]
+name = "docx2txt"
+version = "0.8"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/7d/7d/60ee3f2b16d9bfdfa72e8599470a2c1a5b759cb113c6fe1006be28359327/docx2txt-0.8.tar.gz", hash = "sha256:2c06d98d7cfe2d3947e5760a57d924e3ff07745b379c8737723922e7009236e5", size = 2814 }
+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -706,6 +719,7 @@ version = "0.1.0"
 source = { editable = "." }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "datamodel-code-generator" },
     { name = "events" },
@@ -725,6 +739,7 @@ dev = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../../assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
     { name = "context", editable = "../../../context" },
     { name = "datamodel-code-generator", specifier = ">=0.26.3" },
     { name = "events", editable = "../../../events" },
@@ -1281,7 +1296,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../../openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -1295,7 +1310,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../../assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
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 ]
 
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+version = "20231228"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
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+]
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+version = "0.11.4"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
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+    { name = "pillow" },
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 name = "pexpect"
 version = "4.9.0"
@@ -1650,6 +1692,26 @@ crypto = [
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 ]
 
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+]
+
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 name = "pyright"
 version = "1.1.389"
@@ -2033,6 +2095,7 @@ version = "0.1.0"
 source = { editable = "../../skill-library" }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -2047,6 +2110,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../../assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
     { name = "context", editable = "../../../context" },
     { name = "events", editable = "../../../events" },
     { name = "openai", specifier = ">=1.16.1" },
diff --git a/libraries/python/skills/skills/posix-skill/uv.lock b/libraries/python/skills/skills/posix-skill/uv.lock
index b2a6a3ec..9a27cadb 100644
--- a/libraries/python/skills/skills/posix-skill/uv.lock
+++ b/libraries/python/skills/skills/posix-skill/uv.lock
@@ -209,6 +209,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
 [package.metadata]
 requires-dist = [
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@@ -485,6 +492,12 @@ wheels = [
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+
 [[package]]
 name = "email-validator"
 version = "2.2.0"
@@ -929,7 +942,7 @@ name = "openai-client"
 version = "0.1.0"
 source = { editable = "../../../openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
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 name = "pyright"
 version = "1.1.389"
@@ -1506,6 +1566,7 @@ version = "0.1.0"
 source = { editable = "../../skill-library" }
 dependencies = [
     { name = "assistant-drive" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -1520,6 +1581,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../../assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
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     { name = "events", editable = "../../../events" },
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index fafd359a..ba243b78 100644
--- a/libraries/python/skills/skills/prospector-skill/uv.lock
+++ b/libraries/python/skills/skills/prospector-skill/uv.lock
@@ -209,6 +209,13 @@ dependencies = [
     { name = "semantic-workbench-assistant" },
 ]
 
+[package.optional-dependencies]
+attachments = [
+    { name = "assistant-drive" },
+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
+
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+
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 name = "email-validator"
 version = "2.2.0"
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 version = "0.1.0"
 source = { editable = "../../../openai-client" }
 dependencies = [
-    { name = "assistant-extensions" },
+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -943,7 +956,7 @@ dependencies = [
 
 [package.metadata]
 requires-dist = [
-    { name = "assistant-extensions", editable = "../../../assistant-extensions" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
     { name = "azure-ai-contentsafety", specifier = ">=1.0.0" },
     { name = "azure-core", extras = ["aio"], specifier = ">=1.30.0" },
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 name = "pyright"
 version = "1.1.389"
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 source = { editable = "../../skill-library" }
 dependencies = [
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+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -1520,6 +1581,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../../assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
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     { name = "events", editable = "../../../events" },
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diff --git a/libraries/python/skills/skills/skill-template/uv.lock b/libraries/python/skills/skills/skill-template/uv.lock
index ed90550c..79ea9d37 100644
--- a/libraries/python/skills/skills/skill-template/uv.lock
+++ b/libraries/python/skills/skills/skill-template/uv.lock
@@ -209,6 +209,13 @@ dependencies = [
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 ]
 
+[package.optional-dependencies]
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+    { name = "docx2txt" },
+    { name = "pdfplumber" },
+]
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 version = "2.2.0"
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 source = { editable = "../../../openai-client" }
 dependencies = [
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+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "azure-ai-contentsafety" },
     { name = "azure-core", extra = ["aio"] },
     { name = "azure-identity" },
@@ -943,7 +956,7 @@ dependencies = [
 
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+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
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@@ -1194,6 +1234,26 @@ crypto = [
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@@ -1479,6 +1539,7 @@ version = "0.1.0"
 source = { editable = "../../skill-library" }
 dependencies = [
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+    { name = "assistant-extensions", extra = ["attachments"] },
     { name = "context" },
     { name = "events" },
     { name = "openai" },
@@ -1493,6 +1554,7 @@ dependencies = [
 [package.metadata]
 requires-dist = [
     { name = "assistant-drive", editable = "../../../assistant-drive" },
+    { name = "assistant-extensions", extras = ["attachments"], editable = "../../../assistant-extensions" },
     { name = "context", editable = "../../../context" },
     { name = "events", editable = "../../../events" },
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