diff --git a/api/include/opentelemetry/context/runtime_context.h b/api/include/opentelemetry/context/runtime_context.h
index e60a8726ea..094e1a5bd9 100644
--- a/api/include/opentelemetry/context/runtime_context.h
+++ b/api/include/opentelemetry/context/runtime_context.h
@@ -175,15 +175,30 @@ class ThreadLocalContextStorage : public RuntimeContextStorage
   // Return the current context.
   Context GetCurrent() noexcept override { return GetStack().Top(); }
 
-  // Resets the context to a previous value stored in the
-  // passed in token. Returns true if successful, false otherwise
+  // Resets the context to the value previous to the passed in token. This will
+  // also detach all child contexts of the passed in token.
+  // Returns true if successful, false otherwise.
   bool Detach(Token &token) noexcept override
   {
-    if (!(token == GetStack().Top()))
+    // In most cases, the context to be detached is on the top of the stack.
+    if (token == GetStack().Top())
+    {
+      GetStack().Pop();
+      return true;
+    }
+
+    if (!GetStack().Contains(token))
     {
       return false;
     }
+
+    while (!(token == GetStack().Top()))
+    {
+      GetStack().Pop();
+    }
+
     GetStack().Pop();
+
     return true;
   }
 
@@ -214,6 +229,19 @@ class ThreadLocalContextStorage : public RuntimeContextStorage
       return base_[size_];
     }
 
+    bool Contains(const Token &token) const noexcept
+    {
+      for (size_t pos = size_; pos > 0; --pos)
+      {
+        if (token == base_[pos - 1])
+        {
+          return true;
+        }
+      }
+
+      return false;
+    }
+
     // Returns the Context at the top of the stack.
     Context Top() const noexcept
     {
diff --git a/api/test/context/runtime_context_test.cc b/api/test/context/runtime_context_test.cc
index 31c7d64a8e..3fe78ade44 100644
--- a/api/test/context/runtime_context_test.cc
+++ b/api/test/context/runtime_context_test.cc
@@ -11,7 +11,7 @@ TEST(RuntimeContextTest, GetCurrent)
   std::map<std::string, context::ContextValue> map_test = {{"test_key", (int64_t)123}};
   context::Context test_context                         = context::Context(map_test);
   auto old_context = context::RuntimeContext::Attach(test_context);
-  EXPECT_TRUE(context::RuntimeContext::GetCurrent() == test_context);
+  EXPECT_EQ(context::RuntimeContext::GetCurrent(), test_context);
 }
 
 // Tests that detach resets the context to the previous context
@@ -25,7 +25,7 @@ TEST(RuntimeContextTest, Detach)
   auto foo_context_token  = context::RuntimeContext::Attach(foo_context);
 
   foo_context_token.reset();
-  EXPECT_TRUE(context::RuntimeContext::GetCurrent() == test_context);
+  EXPECT_EQ(context::RuntimeContext::GetCurrent(), test_context);
   test_context_token.reset();
 }
 
@@ -34,9 +34,8 @@ TEST(RuntimeContextTest, DetachWrongContext)
 {
   std::map<std::string, context::ContextValue> map_test = {{"test_key", (int64_t)123}};
   context::Context test_context                         = context::Context(map_test);
-  context::Context foo_context                          = context::Context(map_test);
   auto test_context_token = context::RuntimeContext::Attach(test_context);
-  auto foo_context_token  = context::RuntimeContext::Attach(foo_context);
+  EXPECT_TRUE(context::RuntimeContext::Detach(*test_context_token));
   EXPECT_FALSE(context::RuntimeContext::Detach(*test_context_token));
 }
 
@@ -96,3 +95,38 @@ TEST(RuntimeContextTest, GetValueOtherContext)
   context::Context foo_context = context::Context("foo_key", (int64_t)596);
   EXPECT_EQ(nostd::get<int64_t>(context::RuntimeContext::GetValue("foo_key", &foo_context)), 596);
 }
+
+// Test that any possible order of context detaching doesn't mess up the stack.
+TEST(RuntimeContextTest, DetachOutOfOrder)
+{
+  std::vector<size_t> indices;
+  indices.push_back(0);
+  indices.push_back(1);
+  indices.push_back(2);
+  indices.push_back(3);
+
+  std::vector<context::Context> contexts;
+  for (auto i : indices)
+  {
+    contexts.push_back(context::Context("index", i));
+  }
+
+  do
+  {
+    std::vector<nostd::unique_ptr<context::Token>> tokens;
+
+    for (auto &c : contexts)
+    {
+      tokens.push_back(context::RuntimeContext::Attach(c));
+    }
+
+    for (size_t i : indices)
+    {
+      auto token = std::move(tokens.at(i));
+      context::RuntimeContext::Detach(*token);
+    }
+
+    EXPECT_EQ(context::RuntimeContext::GetCurrent(), context::Context());
+
+  } while (std::next_permutation(indices.begin(), indices.end()));
+}