diff --git a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
index bacd99e967542..c05090d02622f 100644
--- a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
+++ b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
@@ -92,16 +92,6 @@ afterAll(() => {
 })
 
 describe("WorkspacePage", () => {
-  it("requests a stop job when the user presses Stop", async () => {
-    const stopWorkspaceMock = jest
-      .spyOn(api, "stopWorkspace")
-      .mockResolvedValueOnce(MockWorkspaceBuild)
-    testButton(
-      t("actionButton.stop", { ns: "workspacePage" }),
-      stopWorkspaceMock,
-    )
-  })
-
   it("requests a delete job when the user presses Delete and confirms", async () => {
     const user = userEvent.setup()
     const deleteWorkspaceMock = jest
@@ -140,11 +130,23 @@ describe("WorkspacePage", () => {
     const startWorkspaceMock = jest
       .spyOn(api, "startWorkspace")
       .mockImplementation(() => Promise.resolve(MockWorkspaceBuild))
-    testButton(
+    await testButton(
       t("actionButton.start", { ns: "workspacePage" }),
       startWorkspaceMock,
     )
   })
+
+  it("requests a stop job when the user presses Stop", async () => {
+    const stopWorkspaceMock = jest
+      .spyOn(api, "stopWorkspace")
+      .mockResolvedValueOnce(MockWorkspaceBuild)
+
+    await testButton(
+      t("actionButton.stop", { ns: "workspacePage" }),
+      stopWorkspaceMock,
+    )
+  })
+
   it("requests cancellation when the user presses Cancel", async () => {
     server.use(
       rest.get(
diff --git a/site/src/xServices/workspace/workspaceXService.ts b/site/src/xServices/workspace/workspaceXService.ts
index 83111dc2a0a9f..c01691ba6ef17 100644
--- a/site/src/xServices/workspace/workspaceXService.ts
+++ b/site/src/xServices/workspace/workspaceXService.ts
@@ -40,6 +40,27 @@ const moreBuildsAvailable = (
   return event.data.latest_build.updated_at !== latestBuildInTimeline.updated_at
 }
 
+const updateWorkspaceStatus = (
+  status: TypesGen.WorkspaceStatus,
+  workspace?: TypesGen.Workspace,
+) => {
+  if (!workspace) {
+    throw new Error("Workspace not defined")
+  }
+
+  return {
+    ...workspace,
+    latest_build: {
+      ...workspace.latest_build,
+      status,
+    },
+  }
+}
+
+const isUpdated = (newDateStr: string, oldDateStr: string): boolean => {
+  return new Date(oldDateStr).getTime() - new Date(newDateStr).getTime() > 0
+}
+
 const Language = {
   getTemplateWarning:
     "Error updating workspace: latest template could not be fetched.",
@@ -252,6 +273,7 @@ export const workspaceMachine = createMachine(
                 on: {
                   REFRESH_WORKSPACE: {
                     actions: ["refreshWorkspace"],
+                    cond: "hasUpdates",
                   },
                   EVENT_SOURCE_ERROR: {
                     target: "error",
@@ -325,7 +347,7 @@ export const workspaceMachine = createMachine(
                 },
               },
               requestingStart: {
-                entry: "clearBuildError",
+                entry: ["clearBuildError", "updateStatusToStarting"],
                 invoke: {
                   src: "startWorkspace",
                   id: "startWorkspace",
@@ -344,7 +366,7 @@ export const workspaceMachine = createMachine(
                 },
               },
               requestingStop: {
-                entry: "clearBuildError",
+                entry: ["clearBuildError", "updateStatusToStopping"],
                 invoke: {
                   src: "stopWorkspace",
                   id: "stopWorkspace",
@@ -363,7 +385,7 @@ export const workspaceMachine = createMachine(
                 },
               },
               requestingDelete: {
-                entry: "clearBuildError",
+                entry: ["clearBuildError", "updateStatusToDeleting"],
                 invoke: {
                   src: "deleteWorkspace",
                   id: "deleteWorkspace",
@@ -382,7 +404,11 @@ export const workspaceMachine = createMachine(
                 },
               },
               requestingCancel: {
-                entry: ["clearCancellationMessage", "clearCancellationError"],
+                entry: [
+                  "clearCancellationMessage",
+                  "clearCancellationError",
+                  "updateStatusToCanceling",
+                ],
                 invoke: {
                   src: "cancelWorkspace",
                   id: "cancelWorkspace",
@@ -430,9 +456,7 @@ export const workspaceMachine = createMachine(
                 on: {
                   REFRESH_TIMELINE: {
                     target: "#workspaceState.ready.timeline.gettingBuilds",
-                    cond: {
-                      type: "moreBuildsAvailable",
-                    },
+                    cond: "moreBuildsAvailable",
                   },
                 },
               },
@@ -599,9 +623,46 @@ export const workspaceMachine = createMachine(
         }),
         { to: "scheduleBannerMachine" },
       ),
+      // Optimistically updates. So when the user clicks on stop, we can show
+      // the "stopping" state right away without having to wait 0.5s ~ 2s to
+      // display the visual feedback to the user.
+      updateStatusToStarting: assign({
+        workspace: ({ workspace }) =>
+          updateWorkspaceStatus("starting", workspace),
+      }),
+      updateStatusToStopping: assign({
+        workspace: ({ workspace }) =>
+          updateWorkspaceStatus("stopping", workspace),
+      }),
+      updateStatusToDeleting: assign({
+        workspace: ({ workspace }) =>
+          updateWorkspaceStatus("deleting", workspace),
+      }),
+      updateStatusToCanceling: assign({
+        workspace: ({ workspace }) =>
+          updateWorkspaceStatus("canceling", workspace),
+      }),
     },
     guards: {
       moreBuildsAvailable,
+      // We only want to update the workspace when there are changes to it to
+      // avoid re-renderings and allow optimistically updates to improve the UI.
+      // When updating the workspace every second, the optimistic updates that
+      // were applied before get lost since it will be rewrite.
+      hasUpdates: ({ workspace }, event: { data: TypesGen.Workspace }) => {
+        if (!workspace) {
+          throw new Error("Workspace not defined")
+        }
+        const isWorkspaceUpdated = isUpdated(
+          event.data.updated_at,
+          workspace.updated_at,
+        )
+        const isBuildUpdated = isUpdated(
+          event.data.latest_build.updated_at,
+          workspace.latest_build.updated_at,
+        )
+        return isWorkspaceUpdated || isBuildUpdated
+      },
     },
     services: {
       getWorkspace: async (_, event) => {