diff --git a/cli/schedule_test.go b/cli/schedule_test.go
index bc473279f7..ed9c5b1743 100644
--- a/cli/schedule_test.go
+++ b/cli/schedule_test.go
@@ -352,8 +352,6 @@ func TestScheduleOverride(t *testing.T) {
 			require.NoError(t, err, "invalid schedule")
 			ownerClient, _, _, ws := setupTestSchedule(t, sched)
 			now := time.Now()
-			// To avoid the likelihood of time-related flakes, only matching up to the hour.
-			expectedDeadline := now.In(loc).Add(10 * time.Hour).Format("2006-01-02T15:")
 
 			// When: we override the stop schedule
 			inv, root := clitest.New(t,
@@ -364,6 +362,19 @@ func TestScheduleOverride(t *testing.T) {
 			pty := ptytest.New(t).Attach(inv)
 			require.NoError(t, inv.Run())
 
+			// Fetch the workspace to get the actual deadline set by the
+			// server. Computing our own expected deadline from a separately
+			// captured time.Now() is racy: the CLI command calls time.Now()
+			// internally, and with the Asia/Kolkata +05:30 offset the hour
+			// boundary falls at :30 UTC minutes. A small delay between our
+			// time.Now() and the command's is enough to land in different
+			// hours.
+			updated, err := ownerClient.Workspace(context.Background(), ws[0].ID)
+			require.NoError(t, err)
+			require.False(t, updated.LatestBuild.Deadline.IsZero(), "deadline should be set after extend")
+			require.WithinDuration(t, now.Add(10*time.Hour), updated.LatestBuild.Deadline.Time, 5*time.Minute)
+			expectedDeadline := updated.LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339)
+
 			// Then: the updated schedule should be shown
 			pty.ExpectMatch(ws[0].OwnerName + "/" + ws[0].Name)
 			pty.ExpectMatch(sched.Humanize())