diff --git a/.vscode/settings.json b/.vscode/settings.json
index ca19998fa6..b63792e247 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -33,6 +33,7 @@
     "enablements",
     "errgroup",
     "eventsourcemock",
+    "Failf",
     "fatih",
     "Formik",
     "gitauth",
@@ -160,10 +161,7 @@
     "xstate",
     "yamux"
   ],
-  "cSpell.ignorePaths": [
-    "site/package.json",
-    ".vscode/settings.json"
-  ],
+  "cSpell.ignorePaths": ["site/package.json", ".vscode/settings.json"],
   "emeraldwalk.runonsave": {
     "commands": [
       {
@@ -195,10 +193,7 @@
   // To reduce redundancy in tests, it's covered by other packages.
   // Since package coverage pairing can't be defined, all packages cover
   // all other packages.
-  "go.testFlags": [
-    "-short",
-    "-coverpkg=./..."
-  ],
+  "go.testFlags": ["-short", "-coverpkg=./..."],
   // We often use a version of TypeScript that's ahead of the version shipped
   // with VS Code.
   "typescript.tsdk": "./site/node_modules/typescript/lib"
diff --git a/coderd/provisionerdserver/provisionerdserver.go b/coderd/provisionerdserver/provisionerdserver.go
index 240d042ee5..e14d6bbc3d 100644
--- a/coderd/provisionerdserver/provisionerdserver.go
+++ b/coderd/provisionerdserver/provisionerdserver.go
@@ -14,6 +14,8 @@ import (
 
 	"github.com/google/uuid"
 	"github.com/tabbed/pqtype"
+	"golang.org/x/exp/maps"
+	"golang.org/x/exp/slices"
 	"golang.org/x/xerrors"
 	protobuf "google.golang.org/protobuf/proto"
 
@@ -631,14 +633,58 @@ func (server *Server) CompleteJob(ctx context.Context, completed *proto.Complete
 			if err != nil {
 				return xerrors.Errorf("update workspace build: %w", err)
 			}
+
+			agentTimeouts := make(map[time.Duration]bool) // A set of agent timeouts.
 			// This could be a bulk insert to improve performance.
 			for _, protoResource := range jobType.WorkspaceBuild.Resources {
+				for _, protoAgent := range protoResource.Agents {
+					dur := time.Duration(protoAgent.GetConnectionTimeoutSeconds()) * time.Second
+					agentTimeouts[dur] = true
+				}
 				err = InsertWorkspaceResource(ctx, db, job.ID, workspaceBuild.Transition, protoResource, telemetrySnapshot)
 				if err != nil {
 					return xerrors.Errorf("insert provisioner job: %w", err)
 				}
 			}
 
+			// On start, we want to ensure that workspace agents timeout statuses
+			// are propagated. This method is simple and does not protect against
+			// notifying in edge cases like when a workspace is stopped soon
+			// after being started.
+			//
+			// Agent timeouts could be minutes apart, resulting in an unresponsive
+			// experience, so we'll notify after every unique timeout seconds.
+			if !input.DryRun && workspaceBuild.Transition == database.WorkspaceTransitionStart && len(agentTimeouts) > 0 {
+				timeouts := maps.Keys(agentTimeouts)
+				slices.Sort(timeouts)
+
+				var updates []<-chan time.Time
+				for _, d := range timeouts {
+					server.Logger.Debug(ctx, "triggering workspace notification after agent timeout",
+						slog.F("workspace_build_id", workspaceBuild.ID),
+						slog.F("timeout", d),
+					)
+					// Agents are inserted with `database.Now()`, this triggers a
+					// workspace event approximately after created + timeout seconds.
+					updates = append(updates, time.After(d))
+				}
+				go func() {
+					for _, wait := range updates {
+						// Wait for the next potential timeout to occur. Note that we
+						// can't listen on the context here because we will hang around
+						// after this function has returned. The server also doesn't
+						// have a shutdown signal we can listen to.
+						<-wait
+						if err := server.Pubsub.Publish(codersdk.WorkspaceNotifyChannel(workspaceBuild.WorkspaceID), []byte{}); err != nil {
+							server.Logger.Error(ctx, "workspace notification after agent timeout failed",
+								slog.F("workspace_build_id", workspaceBuild.ID),
+								slog.Error(err),
+							)
+						}
+					}
+				}()
+			}
+
 			if workspaceBuild.Transition != database.WorkspaceTransitionDelete {
 				// This is for deleting a workspace!
 				return nil
diff --git a/coderd/workspaces_test.go b/coderd/workspaces_test.go
index 1711de1ba3..1c9c9fb991 100644
--- a/coderd/workspaces_test.go
+++ b/coderd/workspaces_test.go
@@ -1357,6 +1357,7 @@ func TestWorkspaceWatcher(t *testing.T) {
 							Auth: &proto.Agent_Token{
 								Token: authToken,
 							},
+							ConnectionTimeoutSeconds: 1,
 						}},
 					}},
 				},
@@ -1372,58 +1373,64 @@ func TestWorkspaceWatcher(t *testing.T) {
 
 	wc, err := client.WatchWorkspace(ctx, workspace.ID)
 	require.NoError(t, err)
-	wait := func() {
+
+	// Wait events are easier to debug with timestamped logs.
+	logger := slogtest.Make(t, nil).Named(t.Name()).Leveled(slog.LevelDebug)
+	wait := func(event string) {
 		select {
 		case <-ctx.Done():
-			t.Fail()
+			require.FailNow(t, "timed out waiting for event", event)
 		case <-wc:
+			logger.Info(ctx, "done waiting for event", slog.F("event", event))
 		}
 	}
 
 	coderdtest.CreateWorkspaceBuild(t, client, workspace, database.WorkspaceTransitionStart)
-	// the workspace build being created
-	wait()
-	// the workspace build being acquired
-	wait()
-	// the workspace build completing
-	wait()
+	wait("workspace build being created")
+	wait("workspace build being acquired")
+	wait("workspace build completing")
+
+	// Unfortunately, this will add ~1s to the test due to the granularity
+	// of agent timeout seconds. However, if we don't do this we won't know
+	// which trigger we received when waiting for connection.
+	//
+	// Note that the first timeout is from `coderdtest.CreateWorkspace` and
+	// the latter is from `coderdtest.CreateWorkspaceBuild`.
+	wait("agent timeout after create")
+	wait("agent timeout after start")
 
 	agentClient := codersdk.New(client.URL)
 	agentClient.SetSessionToken(authToken)
 	agentCloser := agent.New(agent.Options{
 		Client: agentClient,
-		Logger: slogtest.Make(t, nil).Named("agent").Leveled(slog.LevelDebug),
+		Logger: logger.Named("agent"),
 	})
 	defer func() {
 		_ = agentCloser.Close()
 	}()
 
-	// the agent connected
-	wait()
+	wait("agent connected")
 	agentCloser.Close()
-	// the agent disconnected
-	wait()
+	wait("agent disconnected")
 
 	closeFunc.Close()
 	build := coderdtest.CreateWorkspaceBuild(t, client, workspace, database.WorkspaceTransitionStart)
-	// First is for the workspace build itself
-	wait()
+	wait("first is for the workspace build itself")
 	err = client.CancelWorkspaceBuild(ctx, build.ID)
 	require.NoError(t, err)
-	// Second is for the build cancel
-	wait()
+	wait("second is for the build cancel")
 
 	err = client.UpdateWorkspace(ctx, workspace.ID, codersdk.UpdateWorkspaceRequest{
 		Name: "another",
 	})
 	require.NoError(t, err)
-	wait()
+	wait("update workspace name")
 
 	err = client.UpdateActiveTemplateVersion(ctx, template.ID, codersdk.UpdateActiveTemplateVersion{
 		ID: template.ActiveVersionID,
 	})
 	require.NoError(t, err)
-	wait()
+	wait("update active template version")
 
 	cancel()
 }