diff --git a/pkg/skaffold/runner/build_deploy.go b/pkg/skaffold/runner/build_deploy.go
index c66db8ae5c6..3b04131af8f 100644
--- a/pkg/skaffold/runner/build_deploy.go
+++ b/pkg/skaffold/runner/build_deploy.go
@@ -79,12 +79,6 @@ func (r *SkaffoldRunner) Build(ctx context.Context, out io.Writer, artifacts []*
 		return nil, err
 	}
 
-	if !r.runCtx.SkipTests() {
-		if err = r.tester.Test(ctx, out, bRes); err != nil {
-			return nil, err
-		}
-	}
-
 	// Update which images are logged.
 	r.addTagsToPodSelector(bRes)
 
diff --git a/pkg/skaffold/runner/build_deploy_test.go b/pkg/skaffold/runner/build_deploy_test.go
index 1a541e0a0a6..242cc2ee1c2 100644
--- a/pkg/skaffold/runner/build_deploy_test.go
+++ b/pkg/skaffold/runner/build_deploy_test.go
@@ -139,7 +139,10 @@ func TestBuildTestDeploy(t *testing.T) {
 			runner := createRunner(t, test.testBench, nil, artifacts)
 			bRes, err := runner.Build(ctx, ioutil.Discard, artifacts)
 			if err == nil {
-				err = runner.DeployAndLog(ctx, ioutil.Discard, bRes)
+				err = runner.Test(ctx, ioutil.Discard, bRes)
+				if err == nil {
+					err = runner.DeployAndLog(ctx, ioutil.Discard, bRes)
+				}
 			}
 
 			t.CheckErrorAndDeepEqual(test.shouldErr, err, test.expectedActions, test.testBench.Actions())
diff --git a/pkg/skaffold/runner/dev.go b/pkg/skaffold/runner/dev.go
index c50bccbec9d..a4f6c199e7c 100644
--- a/pkg/skaffold/runner/dev.go
+++ b/pkg/skaffold/runner/dev.go
@@ -102,11 +102,20 @@ func (r *SkaffoldRunner) doDev(ctx context.Context, out io.Writer, logger *kuber
 			instrumentation.AddDevIteration("build")
 			meterUpdated = true
 		}
-		if _, err := r.Build(ctx, out, r.changeSet.needsRebuild); err != nil {
-			logrus.Warnln("Skipping deploy due to error:", err)
+		bRes, err := r.Build(ctx, out, r.changeSet.needsRebuild)
+		if err != nil {
+			logrus.Warnln("Skipping test and deploy due to build error:", err)
 			event.DevLoopFailedInPhase(r.devIteration, sErrors.Build, err)
 			return nil
 		}
+		// TODO(modali): Add skipTest boolean to Tester itself to avoid this check.
+		if !r.runCtx.SkipTests() {
+			if err = r.Test(ctx, out, bRes); err != nil {
+				logrus.Warnln("Skipping deploy due to test error:", err)
+				event.DevLoopFailedInPhase(r.devIteration, sErrors.Build, err)
+				return nil
+			}
+		}
 	}
 
 	if needsDeploy {
@@ -134,7 +143,7 @@ func (r *SkaffoldRunner) doDev(ctx context.Context, out io.Writer, logger *kuber
 	return nil
 }
 
-// Dev watches for changes and runs the skaffold build and deploy
+// Dev watches for changes and runs the skaffold build, test and deploy
 // config until interrupted by the user.
 func (r *SkaffoldRunner) Dev(ctx context.Context, out io.Writer, artifacts []*latest.Artifact) error {
 	event.DevLoopInProgress(r.devIteration)
@@ -219,6 +228,12 @@ func (r *SkaffoldRunner) Dev(ctx context.Context, out io.Writer, artifacts []*la
 		event.DevLoopFailedInPhase(r.devIteration, sErrors.Build, err)
 		return fmt.Errorf("exiting dev mode because first build failed: %w", err)
 	}
+	if !r.runCtx.SkipTests() {
+		if err = r.Test(ctx, out, bRes); err != nil {
+			event.DevLoopFailedInPhase(r.devIteration, sErrors.Build, err)
+			return fmt.Errorf("exiting dev mode because test failed after first build: %w", err)
+		}
+	}
 
 	logger := r.createLogger(out, bRes)
 	defer logger.Stop()