diff --git a/orbit/changes/log-time-format b/orbit/changes/log-time-format
new file mode 100644
index 0000000000..00fed61b88
--- /dev/null
+++ b/orbit/changes/log-time-format
@@ -0,0 +1 @@
+* Fixed a log timestamp to print the right duration value when a fleet update has exceeded the maximum number of retries.
diff --git a/pkg/retry/limited_with_cooldown.go b/pkg/retry/limited_with_cooldown.go
index fc0c55015b..350b1e50fe 100644
--- a/pkg/retry/limited_with_cooldown.go
+++ b/pkg/retry/limited_with_cooldown.go
@@ -64,7 +64,7 @@ func (t *LimitedWithCooldown) Do(hash string, fn func() error) error {
 
 	if t.retries[hash] >= t.maxRetries &&
 		time.Since(t.wait[hash]) <= t.cooldown {
-		return &ExcessRetriesError{nextRetry: time.Until(t.wait[hash])}
+		return &ExcessRetriesError{nextRetry: time.Until(t.wait[hash].Add(t.cooldown))}
 	}
 
 	if err := fn(); err != nil {
diff --git a/pkg/retry/limited_with_cooldown_test.go b/pkg/retry/limited_with_cooldown_test.go
index 48dbb6f608..d6887d358e 100644
--- a/pkg/retry/limited_with_cooldown_test.go
+++ b/pkg/retry/limited_with_cooldown_test.go
@@ -51,7 +51,8 @@ func TestLimitedWithCooldwonDo(t *testing.T) {
 	})
 
 	t.Run("exceed max retries", func(t *testing.T) {
-		lwc := NewLimitedWithCooldown(3, 1*time.Hour)
+		cooldown := 1 * time.Hour
+		lwc := NewLimitedWithCooldown(3, cooldown)
 		hash := "foo"
 
 		for i := 0; i < 3; i++ {
@@ -64,8 +65,9 @@ func TestLimitedWithCooldwonDo(t *testing.T) {
 		err := lwc.Do(hash, func() error {
 			return nil
 		})
-		var rErr *ExcessRetriesError
-		require.ErrorAs(t, err, &rErr)
+		rErr, ok := err.(*ExcessRetriesError)
+		require.True(t, ok)
+		require.WithinDuration(t, time.Now().Add(cooldown), time.Now().Add(rErr.nextRetry), 1*time.Minute)
 	})
 
 	t.Run("cooldown period", func(t *testing.T) {