diff --git a/cli/list_test.go b/cli/list_test.go
index 597e4451a9140..8343f1fead1ab 100644
--- a/cli/list_test.go
+++ b/cli/list_test.go
@@ -16,8 +16,6 @@ func TestList(t *testing.T) {
 	t.Parallel()
 	t.Run("Single", func(t *testing.T) {
 		t.Parallel()
-		ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
-		defer cancelFunc()
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
 		user := coderdtest.CreateFirstUser(t, client)
 		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
@@ -30,6 +28,9 @@ func TestList(t *testing.T) {
 		pty := ptytest.New(t)
 		cmd.SetIn(pty.Input())
 		cmd.SetOut(pty.Output())
+
+		ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
+		defer cancelFunc()
 		done := make(chan any)
 		go func() {
 			errC := cmd.ExecuteContext(ctx)
diff --git a/coderd/provisionerjobs_internal_test.go b/coderd/provisionerjobs_internal_test.go
index 2a9914887227a..b09cd3d623d37 100644
--- a/coderd/provisionerjobs_internal_test.go
+++ b/coderd/provisionerjobs_internal_test.go
@@ -27,8 +27,6 @@ func TestProvisionerJobLogs_Unit(t *testing.T) {
 	t.Parallel()
 
 	t.Run("QueryPubSubDupes", func(t *testing.T) {
-		ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
-		t.Cleanup(cancel)
 		logger := slogtest.Make(t, nil).Leveled(slog.LevelDebug)
 		// mDB := mocks.NewStore(t)
 		fDB := databasefake.New()
@@ -65,6 +63,9 @@ func TestProvisionerJobLogs_Unit(t *testing.T) {
 			{ID: uuid.New(), JobID: jobID, Stage: "Stage3"},
 		}
 
+		ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+		defer cancel()
+
 		// wow there are a lot of DB rows we touch...
 		_, err = fDB.InsertAPIKey(ctx, database.InsertAPIKeyParams{
 			ID:           keyID,
diff --git a/site/site_test.go b/site/site_test.go
index 3c5ffb7068450..27b6edcbbf527 100644
--- a/site/site_test.go
+++ b/site/site_test.go
@@ -48,7 +48,7 @@ func TestCaching(t *testing.T) {
 	defer srv.Close()
 
 	// Create a context
-	ctx, cancelFunc := context.WithTimeout(context.Background(), 1*time.Second)
+	ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
 	defer cancelFunc()
 
 	testCases := []struct {
@@ -108,7 +108,7 @@ func TestServingFiles(t *testing.T) {
 	defer srv.Close()
 
 	// Create a context
-	ctx, cancelFunc := context.WithTimeout(context.Background(), 1*time.Second)
+	ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
 	defer cancelFunc()
 
 	testCases := []struct {
@@ -337,7 +337,7 @@ func TestServingBin(t *testing.T) {
 			defer srv.Close()
 
 			// Create a context
-			ctx, cancelFunc := context.WithTimeout(context.Background(), 1*time.Second)
+			ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
 			defer cancelFunc()
 
 			for _, tr := range tt.reqs {