diff --git a/site/src/components/DropdownButton/ActionCtas.tsx b/site/src/components/DropdownButton/ActionCtas.tsx
index 7f104da3833dd..0186797a9703d 100644
--- a/site/src/components/DropdownButton/ActionCtas.tsx
+++ b/site/src/components/DropdownButton/ActionCtas.tsx
@@ -160,7 +160,6 @@ const useStyles = makeStyles((theme) => ({
   // this is all custom to work with our button wrapper
   loadingButton: {
     border: "none",
-    borderLeft: "1px solid #333740", // MUI disabled button
-    borderRadius: "3px 0px 0px 3px",
+    borderRadius: `${theme.shape.borderRadius} 0px 0px ${theme.shape.borderRadius}`,
   },
 }))
diff --git a/site/src/components/DropdownButton/DropdownButton.tsx b/site/src/components/DropdownButton/DropdownButton.tsx
index f7ffcdbb187b7..c4067f9293ecc 100644
--- a/site/src/components/DropdownButton/DropdownButton.tsx
+++ b/site/src/components/DropdownButton/DropdownButton.tsx
@@ -95,7 +95,7 @@ const useStyles = makeStyles((theme) => ({
     borderLeft: `1px solid ${theme.palette.divider}`,
     borderRadius: `0px ${theme.shape.borderRadius}px ${theme.shape.borderRadius}px 0px`,
     minWidth: "unset",
-    width: "63px", // matching cancel button so button grouping doesn't grow in size
+    width: "64px", // matching cancel button so button grouping doesn't grow in size
     "& .MuiButton-label": {
       marginRight: "8px",
     },
diff --git a/site/src/components/LoadingButton/LoadingButton.tsx b/site/src/components/LoadingButton/LoadingButton.tsx
index 6efb4e4aa7f7e..60c0d4997bc31 100644
--- a/site/src/components/LoadingButton/LoadingButton.tsx
+++ b/site/src/components/LoadingButton/LoadingButton.tsx
@@ -31,7 +31,7 @@ export const LoadingButton: FC<React.PropsWithChildren<LoadingButtonProps>> = ({
       <span style={hidden}>{children}</span>
       {loading && (
         <div className={styles.loader}>
-          <CircularProgress size={18} className={styles.spinner} />
+          <CircularProgress size={16} className={styles.spinner} />
         </div>
       )}
       {Boolean(loadingLabel) && loadingLabel}
@@ -63,7 +63,7 @@ const useStyles = makeStyles<Theme, StyleProps>((theme) => ({
     top: "50%",
     left: "50%",
     height: 22, // centering loading icon
-    width: 18,
+    width: 16,
   },
   spinner: {
     color: theme.palette.text.disabled,
diff --git a/site/src/components/WorkspaceActions/WorkspaceActions.tsx b/site/src/components/WorkspaceActions/WorkspaceActions.tsx
index 66b6a18d9278a..503ae6e7947d6 100644
--- a/site/src/components/WorkspaceActions/WorkspaceActions.tsx
+++ b/site/src/components/WorkspaceActions/WorkspaceActions.tsx
@@ -64,7 +64,7 @@ export const WorkspaceActions: FC<WorkspaceActionsProps> = ({
       <DisabledButton label={t("disabledButton.deleted")} />
     ),
     [ButtonTypesEnum.pending]: (
-      <DisabledButton label={t("disabledButton.pending")} />
+      <ActionLoadingButton label={t("disabledButton.pending")} />
     ),
   }
 
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..13b8afa1b8b77 100644
--- a/site/src/xServices/workspace/workspaceXService.ts
+++ b/site/src/xServices/workspace/workspaceXService.ts
@@ -325,7 +325,7 @@ export const workspaceMachine = createMachine(
                 },
               },
               requestingStart: {
-                entry: "clearBuildError",
+                entry: ["clearBuildError", "updateStatusToPending"],
                 invoke: {
                   src: "startWorkspace",
                   id: "startWorkspace",
@@ -344,7 +344,7 @@ export const workspaceMachine = createMachine(
                 },
               },
               requestingStop: {
-                entry: "clearBuildError",
+                entry: ["clearBuildError", "updateStatusToPending"],
                 invoke: {
                   src: "stopWorkspace",
                   id: "stopWorkspace",
@@ -363,7 +363,7 @@ export const workspaceMachine = createMachine(
                 },
               },
               requestingDelete: {
-                entry: "clearBuildError",
+                entry: ["clearBuildError", "updateStatusToPending"],
                 invoke: {
                   src: "deleteWorkspace",
                   id: "deleteWorkspace",
@@ -382,7 +382,11 @@ export const workspaceMachine = createMachine(
                 },
               },
               requestingCancel: {
-                entry: ["clearCancellationMessage", "clearCancellationError"],
+                entry: [
+                  "clearCancellationMessage",
+                  "clearCancellationError",
+                  "updateStatusToPending",
+                ],
                 invoke: {
                   src: "cancelWorkspace",
                   id: "cancelWorkspace",
@@ -430,9 +434,7 @@ export const workspaceMachine = createMachine(
                 on: {
                   REFRESH_TIMELINE: {
                     target: "#workspaceState.ready.timeline.gettingBuilds",
-                    cond: {
-                      type: "moreBuildsAvailable",
-                    },
+                    cond: "moreBuildsAvailable",
                   },
                 },
               },
@@ -599,6 +601,24 @@ export const workspaceMachine = createMachine(
         }),
         { to: "scheduleBannerMachine" },
       ),
+      // Optimistically update. So when the user clicks on stop, we can show
+      // the "pending" state right away without having to wait 0.5s ~ 2s to
+      // display the visual feedback to the user.
+      updateStatusToPending: assign({
+        workspace: ({ workspace }) => {
+          if (!workspace) {
+            throw new Error("Workspace not defined")
+          }
+
+          return {
+            ...workspace,
+            latest_build: {
+              ...workspace.latest_build,
+              status: "pending" as TypesGen.WorkspaceStatus,
+            },
+          }
+        },
+      }),
     },
     guards: {
       moreBuildsAvailable,