diff --git a/test/test_license.py b/test/test_license.py
index 0c5a72c1e..4656625cd 100644
--- a/test/test_license.py
+++ b/test/test_license.py
@@ -408,8 +408,11 @@ class TestLicense(unittest.TestCase):
                         expired=ExpirationType.trial_only)
 
   def test_valid_regions_across_multiple_sub_one_expired(self):
+    service_end = get_date(timedelta(days=20))
+    expiration_date = get_date(timedelta(days=10))
+
     license = self.create_license({
-      "expirationDate": get_date(timedelta(days=10)),
+      "expirationDate": expiration_date,
       "subscriptions": {
         "somesub": {
           "trialEnd": get_date(TRIAL_GRACE_PERIOD * -1 + timedelta(days=-1)),
@@ -420,7 +423,7 @@ class TestLicense(unittest.TestCase):
           },
         },
         "anothersub": {
-          "serviceEnd": get_date(timedelta(days=20)),
+          "serviceEnd": service_end,
           "entitlements": {
             QUAY_ENTITLEMENT: 1,
             QUAY_DEPLOYMENTS_ENTITLEMENT: 5,
@@ -438,6 +441,12 @@ class TestLicense(unittest.TestCase):
 
     self.assertValid(license, config=config)
 
+    entitlements = license.validate(config)
+    self.assertEquals(2, len(entitlements))
+
+    self.assertEntitlement(entitlements[0], QUAY_ENTITLEMENT, expiration_date)
+    self.assertEntitlement(entitlements[1], QUAY_DEPLOYMENTS_ENTITLEMENT, expiration_date)
+
   def test_quay_is_under_expired_sub(self):
     license = self.create_license({
       "expirationDate": get_date(timedelta(days=10)),
@@ -469,6 +478,93 @@ class TestLicense(unittest.TestCase):
     self.assertNotValid(license, config=config, expired=ExpirationType.trial_only,
                         requirement=QUAY_ENTITLEMENT)
 
+  def assertEntitlement(self, entitlement, expected_name, expected_date):
+    self.assertEquals(expected_name, entitlement.requirement.name)
+    self.assertEquals(expected_date, str(entitlement.entitlement.expiration.expiration_date))
+
+  def test_license_with_multiple_subscriptions(self):
+    service_end = get_date(timedelta(days=20))
+    expiration_date = get_date(timedelta(days=10))
+    trial_end = get_date(timedelta(days=2))
+
+    license = self.create_license({
+      "expirationDate": expiration_date,
+      "subscriptions": {
+        "realsub": {
+          "serviceEnd": service_end,
+          "entitlements": {
+            QUAY_ENTITLEMENT: 1,
+          },
+        },
+        "trialsub": {
+          "trialEnd": trial_end,
+          "trialOnly": True,
+          "inTrial": True,
+          "entitlements": {
+            QUAY_ENTITLEMENT: 1,
+            QUAY_DEPLOYMENTS_ENTITLEMENT: 3,
+          },
+        },
+      },
+    })
+
+    config = {
+      'DISTRIBUTED_STORAGE_CONFIG': [
+        {'name': 'first'},
+        {'name': 'second'},
+      ],
+    }
+
+    self.assertValid(license, config=config)
+
+    entitlements = license.validate(config)
+    self.assertEquals(2, len(entitlements))
+
+    self.assertEntitlement(entitlements[0], QUAY_ENTITLEMENT, expiration_date)
+    self.assertEntitlement(entitlements[1], QUAY_DEPLOYMENTS_ENTITLEMENT, trial_end)
+
+  def test_license_with_multiple_subscriptions_one_expired(self):
+    service_end = get_date(timedelta(days=20))
+    expiration_date = get_date(timedelta(days=10))
+    trial_end = get_date(timedelta(days=-2))
+
+    license = self.create_license({
+      "expirationDate": expiration_date,
+      "subscriptions": {
+        "realsub": {
+          "serviceEnd": service_end,
+          "entitlements": {
+            QUAY_ENTITLEMENT: 1,
+            QUAY_DEPLOYMENTS_ENTITLEMENT: 3,
+          },
+        },
+        "trialsub": {
+          "trialEnd": trial_end,
+          "trialOnly": True,
+          "inTrial": True,
+          "entitlements": {
+            QUAY_ENTITLEMENT: 1,
+            QUAY_DEPLOYMENTS_ENTITLEMENT: 3,
+          },
+        },
+      },
+    })
+
+    config = {
+      'DISTRIBUTED_STORAGE_CONFIG': [
+        {'name': 'first'},
+        {'name': 'second'},
+      ],
+    }
+
+    self.assertValid(license, config=config)
+
+    entitlements = license.validate(config)
+    self.assertEquals(2, len(entitlements))
+
+    self.assertEntitlement(entitlements[0], QUAY_ENTITLEMENT, expiration_date)
+    self.assertEntitlement(entitlements[1], QUAY_DEPLOYMENTS_ENTITLEMENT, expiration_date)
+
 if __name__ == '__main__':
   unittest.main()
 
diff --git a/util/license.py b/util/license.py
index 57def018f..decd6bdbb 100644
--- a/util/license.py
+++ b/util/license.py
@@ -187,6 +187,14 @@ class EntitlementValidationResult(object):
     return self.get_status() == EntitlementStatus.met
 
   def __lt__(self, rhs):
+    # If this result has the same status as another, return the result with an expiration date
+    # further in the future, as it will be more relevant. The results may expire, but so long as
+    # this result is valid, so will the entitlement.
+    if self.get_status() == rhs.get_status():
+      return (self.entitlement.expiration.expiration_date >
+              rhs.entitlement.expiration.expiration_date)
+
+    # Otherwise, sort lexically by status.
     return self.get_status() < rhs.get_status()
 
   def __repr__(self):