diff --git a/sdk/core/azure-core/azure/core/pipeline/policies/_authentication.py b/sdk/core/azure-core/azure/core/pipeline/policies/_authentication.py
index 4af2d9312327..36edd3cbc020 100644
--- a/sdk/core/azure-core/azure/core/pipeline/policies/_authentication.py
+++ b/sdk/core/azure-core/azure/core/pipeline/policies/_authentication.py
@@ -89,9 +89,9 @@ def on_request(self, request):
         """
         self._enforce_https(request)
 
-        if self._need_new_token:
+        if self._token is None or self._need_new_token:
             self._token = self._credential.get_token(*self._scopes)
-            self._update_headers(request.http_request.headers, self._token.token)
+        self._update_headers(request.http_request.headers, self._token.token)
 
 
 class AzureKeyCredentialPolicy(SansIOHTTPPolicy):
diff --git a/sdk/core/azure-core/tests/azure_core_asynctests/test_authentication.py b/sdk/core/azure-core/tests/azure_core_asynctests/test_authentication.py
index 80a5b1333c98..456001b59da5 100644
--- a/sdk/core/azure-core/tests/azure_core_asynctests/test_authentication.py
+++ b/sdk/core/azure-core/tests/azure_core_asynctests/test_authentication.py
@@ -18,7 +18,8 @@
 @pytest.mark.asyncio
 async def test_bearer_policy_adds_header():
     """The bearer token policy should add a header containing a token from its credential"""
-    expected_token = AccessToken("expected_token", 0)
+    # 2524608000 == 01/01/2050 @ 12:00am (UTC)
+    expected_token = AccessToken("expected_token", 2524608000)
 
     async def verify_authorization_header(request):
         assert request.http_request.headers["Authorization"] == "Bearer {}".format(expected_token.token)
@@ -37,6 +38,10 @@ async def get_token(_):
     await pipeline.run(HttpRequest("GET", "https://spam.eggs"), context=None)
     assert get_token_calls == 1
 
+    await pipeline.run(HttpRequest("GET", "https://spam.eggs"), context=None)
+    # Didn't need a new token
+    assert get_token_calls == 1
+
 
 @pytest.mark.asyncio
 async def test_bearer_policy_send():
diff --git a/sdk/core/azure-core/tests/test_authentication.py b/sdk/core/azure-core/tests/test_authentication.py
index 0bfeb55a77c8..fb56819b6451 100644
--- a/sdk/core/azure-core/tests/test_authentication.py
+++ b/sdk/core/azure-core/tests/test_authentication.py
@@ -23,7 +23,8 @@
 
 def test_bearer_policy_adds_header():
     """The bearer token policy should add a header containing a token from its credential"""
-    expected_token = AccessToken("expected_token", 0)
+    # 2524608000 == 01/01/2050 @ 12:00am (UTC)
+    expected_token = AccessToken("expected_token", 2524608000)
 
     def verify_authorization_header(request):
         assert request.http_request.headers["Authorization"] == "Bearer {}".format(expected_token.token)
@@ -31,10 +32,15 @@ def verify_authorization_header(request):
     fake_credential = Mock(get_token=Mock(return_value=expected_token))
     policies = [BearerTokenCredentialPolicy(fake_credential, "scope"), Mock(send=verify_authorization_header)]
 
-    Pipeline(transport=Mock(), policies=policies).run(HttpRequest("GET", "https://spam.eggs"))
+    pipeline = Pipeline(transport=Mock(), policies=policies)
+    pipeline.run(HttpRequest("GET", "https://spam.eggs"))
 
     assert fake_credential.get_token.call_count == 1
 
+    pipeline.run(HttpRequest("GET", "https://spam.eggs"))
+
+    # Didn't need a new token
+    assert fake_credential.get_token.call_count == 1
 
 def test_bearer_policy_send():
     """The bearer token policy should invoke the next policy's send method and return the result"""