diff --git a/cli/support_test.go b/cli/support_test.go
index 274454acb7a48..1fb336142d4be 100644
--- a/cli/support_test.go
+++ b/cli/support_test.go
@@ -45,7 +45,7 @@ func TestSupportBundle(t *testing.T) {
 
 	t.Run("Workspace", func(t *testing.T) {
 		t.Parallel()
-		ctx := testutil.Context(t, testutil.WaitShort)
+
 		var dc codersdk.DeploymentConfig
 		secretValue := uuid.NewString()
 		seedSecretDeploymentOptions(t, &dc, secretValue)
@@ -61,6 +61,8 @@ func TestSupportBundle(t *testing.T) {
 			agents[0].Env["SECRET_VALUE"] = secretValue
 			return agents
 		}).Do()
+
+		ctx := testutil.Context(t, testutil.WaitShort)
 		ws, err := client.Workspace(ctx, r.Workspace.ID)
 		require.NoError(t, err)
 		tempDir := t.TempDir()
@@ -72,6 +74,8 @@ func TestSupportBundle(t *testing.T) {
 		defer agt.Close()
 		coderdtest.NewWorkspaceAgentWaiter(t, client, r.Workspace.ID).Wait()
 
+		ctx = testutil.Context(t, testutil.WaitShort) // Reset timeout after waiting for agent.
+
 		// Insert a provisioner job log
 		_, err = db.InsertProvisionerJobLogs(ctx, database.InsertProvisionerJobLogsParams{
 			JobID:     r.Build.JobID,