diff --git a/scripts/devops_tasks/build_packages.py b/scripts/devops_tasks/build_packages.py
index bc962c29e0a4..3a8d221935b5 100644
--- a/scripts/devops_tasks/build_packages.py
+++ b/scripts/devops_tasks/build_packages.py
@@ -12,7 +12,7 @@
 import sys
 import os
 
-from common_tasks import process_glob_string, run_check_call
+from common_tasks import process_glob_string, run_check_call, str_to_bool
 
 root_dir = os.path.abspath(os.path.join(os.path.abspath(__file__), "..", "..", ".."))
 build_packing_script_location = os.path.join(root_dir, "build_package.py")
@@ -22,17 +22,6 @@
 sys.path.append(tox_path)
 from sanitize_setup import process_requires
 
-
-def str_to_bool(input_string):
-    if isinstance(input_string, bool):
-        return input_string
-    elif input_string.lower() in ("true", "t", "1"):
-        return True
-    elif input_string.lower() in ("false", "f", "0"):
-        return False
-    else:
-        return False
-
 def build_packages(targeted_packages, distribution_directory, is_dev_build=False):
     # run the build and distribution
     for package_root in targeted_packages:
diff --git a/scripts/devops_tasks/common_tasks.py b/scripts/devops_tasks/common_tasks.py
index c0ad19122385..3afb50e3461d 100644
--- a/scripts/devops_tasks/common_tasks.py
+++ b/scripts/devops_tasks/common_tasks.py
@@ -119,6 +119,15 @@ def clean_coverage(coverage_dir):
         else:
             raise
 
+def str_to_bool(input_string):
+    if isinstance(input_string, bool):
+        return input_string
+    elif input_string.lower() in ("true", "t", "1"):
+        return True
+    elif input_string.lower() in ("false", "f", "0"):
+        return False
+    else:
+        return False
 
 def parse_setup(setup_path):
     setup_filename = os.path.join(setup_path, "setup.py")
@@ -399,7 +408,7 @@ def extend_dev_requirements(dev_req_path, packages_to_include):
     # include any package given in included list. omit duplicate
     for requirement in packages_to_include:
         if requirement not in requirements:
-            requirements.append(requirement)
+            requirements.insert(0, requirement.rstrip() + '\n')
 
     logging.info("Extending dev requirements. New result:: {}".format(requirements))
     # create new dev requirements file with different name for filtered requirements
diff --git a/scripts/devops_tasks/test_regression.py b/scripts/devops_tasks/test_regression.py
index 934fbbf5e702..1c69c07cc0a0 100644
--- a/scripts/devops_tasks/test_regression.py
+++ b/scripts/devops_tasks/test_regression.py
@@ -23,7 +23,9 @@
     find_packages_missing_on_pypi,
     find_whl,
     find_tools_packages,
-    get_installed_packages
+    get_installed_packages,
+    extend_dev_requirements,
+    str_to_bool
 )
 from git_helper import get_release_tag, git_checkout_tag, git_checkout_branch, clone_repo
 
@@ -38,6 +40,8 @@
 AZURE_SDK_FOR_PYTHON_GIT_URL = "https://github.com/Azure/azure-sdk-for-python.git"
 TEMP_FOLDER_NAME = ".tmp_code_path"
 
+OLDEST_EXTENSION_PKGS = ['msrestazure','adal']
+
 logging.getLogger().setLevel(logging.INFO)
 
 class CustomVirtualEnv:
@@ -114,6 +118,7 @@ def run(self):
             logging.info("Dependent packages for [{0}]: {1}".format(pkg_name, dep_packages))
             for dep_pkg_path in dep_packages:
                 dep_pkg_name, _, _, _ = parse_setup(dep_pkg_path)
+
                 logging.info(
                     "Starting regression test of {0} against released {1}".format(
                         pkg_name, dep_pkg_name
@@ -235,6 +240,18 @@ def _install_packages(self, dependent_pkg_path, pkg_to_exclude):
             dependent_pkg_path, list_to_exclude, dependent_pkg_path
         )
 
+        # early versions of azure-sdk-tools had an unpinned version of azure-mgmt packages. 
+        # that unpinned version hits an a code path in azure-sdk-tools that hits this error.
+        if filtered_dev_req_path and self.context.is_latest_depend_test == False:
+            logging.info(
+                "Extending dev requirements with {}".format(OLDEST_EXTENSION_PKGS)
+            )
+            extend_dev_requirements(
+                filtered_dev_req_path, OLDEST_EXTENSION_PKGS
+            )
+        else:
+            logging.info("Not extending dev requirements {} {}".format(filtered_dev_req_path, self.context.is_latest_depend_test))
+
         if filtered_dev_req_path:
             logging.info(
                 "Installing filtered dev requirements from {}".format(filtered_dev_req_path)
@@ -289,7 +306,6 @@ def find_package_dependency(glob_string, repo_root_dir):
 
 # This is the main function which identifies packages to test, find dependency matrix and trigger test
 def run_main(args):
-
     temp_dir = ""
     if args.temp_dir:
         temp_dir = args.temp_dir
@@ -318,7 +334,7 @@ def run_main(args):
     if len(targeted_packages) == 0:
         exit(0)
 
-    # clone code repo only if it doesn't exists
+    # clone code repo only if it doesn't exist
     if not os.path.exists(code_repo_root):
         clone_repo(temp_dir, AZURE_SDK_FOR_PYTHON_GIT_URL)
     else:
@@ -333,7 +349,7 @@ def run_main(args):
 
     # Create regression text context. One context object will be reused for all packages
     context = RegressionContext(
-        args.whl_dir, temp_dir, args.verify_latest, args.mark_arg
+        args.whl_dir, temp_dir, str_to_bool(args.verify_latest), args.mark_arg
     )
 
     for pkg_path in targeted_packages: