diff --git a/plugins/database/mssql/mssql_test.go b/plugins/database/mssql/mssql_test.go
index 7718946831..5f8c2964cb 100644
--- a/plugins/database/mssql/mssql_test.go
+++ b/plugins/database/mssql/mssql_test.go
@@ -56,7 +56,7 @@ func TestInitialize(t *testing.T) {
 	for name, test := range tests {
 		t.Run(name, func(t *testing.T) {
 			db := new()
-			dbtesting.AssertInitialize(t, db, test.req)
+			dbtesting.AssertInitializeCircleCiTest(t, db, test.req)
 			defer dbtesting.AssertClose(t, db)
 
 			if !db.Initialized {
@@ -144,7 +144,7 @@ func TestNewUser(t *testing.T) {
 			}
 
 			db := new()
-			dbtesting.AssertInitialize(t, db, initReq)
+			dbtesting.AssertInitializeCircleCiTest(t, db, initReq)
 			defer dbtesting.AssertClose(t, db)
 
 			createResp, err := db.NewUser(context.Background(), test.req)
@@ -250,7 +250,7 @@ func TestUpdateUser_password(t *testing.T) {
 			}
 
 			db := new()
-			dbtesting.AssertInitialize(t, db, initReq)
+			dbtesting.AssertInitializeCircleCiTest(t, db, initReq)
 			defer dbtesting.AssertClose(t, db)
 
 			createTestMSSQLUser(t, connURL, dbUser, initPassword, testMSSQLLogin)
@@ -313,7 +313,8 @@ func TestDeleteUser(t *testing.T) {
 	}
 
 	db := new()
-	dbtesting.AssertInitialize(t, db, initReq)
+
+	dbtesting.AssertInitializeCircleCiTest(t, db, initReq)
 	defer dbtesting.AssertClose(t, db)
 
 	createTestMSSQLUser(t, connURL, dbUser, initPassword, testMSSQLLogin)
diff --git a/sdk/database/dbplugin/v5/testing/test_helpers.go b/sdk/database/dbplugin/v5/testing/test_helpers.go
index a5b4b337e5..e3bee3b07e 100644
--- a/sdk/database/dbplugin/v5/testing/test_helpers.go
+++ b/sdk/database/dbplugin/v5/testing/test_helpers.go
@@ -22,19 +22,47 @@ func getRequestTimeout(t *testing.T) time.Duration {
 	return dur
 }
 
+// AssertInitializeCircleCiTest help to diagnose CircleCI failures within AssertInitialize for mssql tests failing
+// with "Failed to initialize: error verifying connection ...". This will now mark a test as failed instead of being fatal
+func AssertInitializeCircleCiTest(t *testing.T, db dbplugin.Database, req dbplugin.InitializeRequest) dbplugin.InitializeResponse {
+	t.Helper()
+	maxAttempts := 5
+	var resp dbplugin.InitializeResponse
+	var err error
+
+	for i := 1; i <= maxAttempts; i++ {
+		resp, err = verifyInitialize(t, db, req)
+		if err != nil {
+			t.Errorf("Failed AssertInitialize attempt: %d with error:\n%+v\n", i, err)
+			time.Sleep(1 * time.Second)
+			continue
+		}
+
+		if i > 1 {
+			t.Logf("AssertInitialize worked the %d time around with a 1 second sleep", i)
+		}
+		break
+	}
+
+	return resp
+}
+
 func AssertInitialize(t *testing.T, db dbplugin.Database, req dbplugin.InitializeRequest) dbplugin.InitializeResponse {
 	t.Helper()
-
-	ctx, cancel := context.WithTimeout(context.Background(), getRequestTimeout(t))
-	defer cancel()
-
-	resp, err := db.Initialize(ctx, req)
+	resp, err := verifyInitialize(t, db, req)
 	if err != nil {
 		t.Fatalf("Failed to initialize: %s", err)
 	}
 	return resp
 }
 
+func verifyInitialize(t *testing.T, db dbplugin.Database, req dbplugin.InitializeRequest) (dbplugin.InitializeResponse, error) {
+	ctx, cancel := context.WithTimeout(context.Background(), getRequestTimeout(t))
+	defer cancel()
+
+	return db.Initialize(ctx, req)
+}
+
 func AssertNewUser(t *testing.T, db dbplugin.Database, req dbplugin.NewUserRequest) dbplugin.NewUserResponse {
 	t.Helper()