diff --git a/sdk/core/azure-core/CHANGELOG.md b/sdk/core/azure-core/CHANGELOG.md
index d9c4bc78a..9e4cb2280 100644
--- a/sdk/core/azure-core/CHANGELOG.md
+++ b/sdk/core/azure-core/CHANGELOG.md
@@ -6,6 +6,10 @@
 
 - Added support for HTTP conditional requests `MatchConditions` and `RequestConditions`.
 
+### Breaking Changes
+
+- Remove `Context::CancelWhen()`.
+
 ### Bug Fixes
 
 - Fixed computation of the token expiration time in `BearerTokenAuthenticationPolicy`.
diff --git a/sdk/core/azure-core/inc/azure/core/context.hpp b/sdk/core/azure-core/inc/azure/core/context.hpp
index 9acf1cfd0..77c409965 100644
--- a/sdk/core/azure-core/inc/azure/core/context.hpp
+++ b/sdk/core/azure-core/inc/azure/core/context.hpp
@@ -290,6 +290,8 @@ namespace Azure { namespace Core {
     {
     }
 
+    time_point CancelWhen() const;
+
   public:
     /**
      * @brief Construct a new context with no expiration, and no value associated.
@@ -329,11 +331,6 @@ namespace Azure { namespace Core {
           m_contextSharedState, time_point::max(), key, std::move(value))};
     }
 
-    /**
-     * @
-     */
-    time_point CancelWhen() const;
-
     /**
      * @brief Get a value associated with a \p key parameter within this context or the branch of
      * contexts this context belongs to.
diff --git a/sdk/core/azure-core/test/ut/context.cpp b/sdk/core/azure-core/test/ut/context.cpp
index cbb1407b2..5775bae19 100644
--- a/sdk/core/azure-core/test/ut/context.cpp
+++ b/sdk/core/azure-core/test/ut/context.cpp
@@ -81,9 +81,34 @@ TEST(Context, BasicChar)
   EXPECT_TRUE(kind == ContextValue::ContextValueType::StdString);
 }
 
+TEST(Context, ApplicationContext)
+{
+  Context appContext = GetApplicationContext();
+
+  EXPECT_FALSE(appContext.HasKey("Key"));
+  EXPECT_FALSE(appContext.HasKey("key"));
+  EXPECT_FALSE(appContext.HasKey("Value"));
+  EXPECT_FALSE(appContext.HasKey("value"));
+  EXPECT_FALSE(appContext.HasKey("1"));
+  EXPECT_FALSE(appContext.HasKey(""));
+
+  auto duration = std::chrono::milliseconds(250);
+  EXPECT_FALSE(appContext.IsCancelled());
+  std::this_thread::sleep_for(duration);
+  EXPECT_FALSE(appContext.IsCancelled());
+
+  appContext.Cancel();
+  EXPECT_TRUE(appContext.IsCancelled());
+
+  // AppContext2 is the same context as AppContext
+  //  The context should be cancelled
+  Context appContext2 = GetApplicationContext();
+  EXPECT_TRUE(appContext.IsCancelled());
+}
+
 TEST(Context, IsCancelled)
 {
-  auto duration = std::chrono::milliseconds(150);
+  auto duration = std::chrono::milliseconds(250);
   auto deadline = std::chrono::system_clock::now() + duration;
 
   Context context;
@@ -93,6 +118,61 @@ TEST(Context, IsCancelled)
   EXPECT_TRUE(c2.IsCancelled());
 }
 
+TEST(Context, NestedIsCancelled)
+{
+  auto duration = std::chrono::milliseconds(250);
+  auto deadline = std::chrono::system_clock::now() + duration;
+
+  Context context;
+  auto c2 = context.WithValue("Key", "Value");
+  EXPECT_FALSE(c2.IsCancelled());
+  EXPECT_TRUE(c2.HasKey("Key"));
+  EXPECT_FALSE(context.HasKey("Key"));
+
+  auto c3 = context.WithDeadline(deadline);
+  EXPECT_FALSE(context.IsCancelled());
+  EXPECT_FALSE(c2.IsCancelled());
+  EXPECT_FALSE(c3.IsCancelled());
+  std::this_thread::sleep_for(duration);
+
+  EXPECT_FALSE(context.IsCancelled());
+  EXPECT_FALSE(c2.IsCancelled());
+  EXPECT_TRUE(c3.IsCancelled());
+
+  EXPECT_TRUE(c2.HasKey("Key"));
+  EXPECT_FALSE(context.HasKey("Key"));
+  EXPECT_FALSE(c3.HasKey("Key"));
+}
+
+TEST(Context, CancelWithValue)
+{
+  Context context;
+  auto c2 = context.WithValue("Key", "Value");
+  EXPECT_FALSE(context.IsCancelled());
+  EXPECT_FALSE(c2.IsCancelled());
+  EXPECT_TRUE(c2.HasKey("Key"));
+  EXPECT_FALSE(context.HasKey("Key"));
+
+  c2.Cancel();
+  EXPECT_TRUE(c2.IsCancelled());
+  EXPECT_FALSE(context.IsCancelled());
+
+  EXPECT_TRUE(c2.HasKey("Key"));
+  EXPECT_FALSE(context.HasKey("Key"));
+}
+
+TEST(Context, ThrowIfCancelled)
+{
+  auto duration = std::chrono::milliseconds(250);
+  auto deadline = std::chrono::system_clock::now() + duration;
+
+  Context context;
+  auto c2 = context.WithDeadline(deadline);
+  EXPECT_NO_THROW(c2.ThrowIfCancelled());
+  std::this_thread::sleep_for(duration);
+  EXPECT_THROW(c2.ThrowIfCancelled(), Azure::Core::OperationCancelledException);
+}
+
 TEST(Context, Alternative)
 {
   Context context;