diff --git a/changelog/pending/20221212--cli-display--fixes-negative-durations-on-update-display.yaml b/changelog/pending/20221212--cli-display--fixes-negative-durations-on-update-display.yaml
new file mode 100644
index 000000000000..52e79cdf1d34
--- /dev/null
+++ b/changelog/pending/20221212--cli-display--fixes-negative-durations-on-update-display.yaml
@@ -0,0 +1,4 @@
+changes:
+- type: fix
+  scope: cli/display
+  description: Fixes negative durations on update display.
diff --git a/pkg/backend/display/progress.go b/pkg/backend/display/progress.go
index 89296a03b11c..f1bac6d3d749 100644
--- a/pkg/backend/display/progress.go
+++ b/pkg/backend/display/progress.go
@@ -862,6 +862,9 @@ func (display *ProgressDisplay) processNormalEvent(event engine.Event) {
 		// and time elapsed.
 		display.opStopwatch.start[step.URN] = time.Now()
 
+		// Clear out potential event end timings for prior operations on the same resource.
+		delete(display.opStopwatch.end, step.URN)
+
 		row.SetStep(step)
 	} else if event.Type == engine.ResourceOutputsEvent {
 		isRefresh := display.getStepOp(row.Step()) == deploy.OpRefresh