diff --git a/coderd/workspaceagents.go b/coderd/workspaceagents.go
index 7cf62d07ebd91..96f8d570e8152 100644
--- a/coderd/workspaceagents.go
+++ b/coderd/workspaceagents.go
@@ -915,7 +915,9 @@ func convertWorkspaceAgent(derpMap *tailcfg.DERPMap, coordinator tailnet.Coordin
 			// to start up.
 			workspaceAgent.Status = codersdk.WorkspaceAgentConnecting
 		}
-	case dbAgent.DisconnectedAt.Time.After(dbAgent.LastConnectedAt.Time):
+	// We check before instead of after because last connected at and
+	// disconnected at can be equal timestamps in tight-timed tests.
+	case !dbAgent.DisconnectedAt.Time.Before(dbAgent.LastConnectedAt.Time):
 		// If we've disconnected after our last connection, we know the
 		// agent is no longer connected.
 		workspaceAgent.Status = codersdk.WorkspaceAgentDisconnected
diff --git a/coderd/workspaces_test.go b/coderd/workspaces_test.go
index 54b9aaf3cf049..682335dc6d5c8 100644
--- a/coderd/workspaces_test.go
+++ b/coderd/workspaces_test.go
@@ -1402,8 +1402,12 @@ func TestWorkspaceUpdateTTL(t *testing.T) {
 
 			require.Equal(t, testCase.ttlMillis, updated.TTLMillis, "expected autostop ttl to equal requested")
 
-			require.Len(t, auditor.AuditLogs, 7)
-			assert.Equal(t, database.AuditActionWrite, auditor.AuditLogs[6].Action)
+			require.Eventually(t, func() bool {
+				if len(auditor.AuditLogs) != 7 {
+					return false
+				}
+				return auditor.AuditLogs[6].Action == database.AuditActionWrite
+			}, testutil.WaitMedium, testutil.IntervalFast, "expected audit log to be written")
 		})
 	}