diff --git a/site/src/api/api.ts b/site/src/api/api.ts
index 8b763bb644595..3cd0d3a7ec29c 100644
--- a/site/src/api/api.ts
+++ b/site/src/api/api.ts
@@ -1,4 +1,5 @@
 import axios, { AxiosRequestHeaders } from "axios"
+import * as Types from "./types"
 import { WorkspaceBuildTransition } from "./types"
 import * as TypesGen from "./typesGenerated"
 
@@ -161,6 +162,11 @@ export const startWorkspace = postWorkspaceBuild("start")
 export const stopWorkspace = postWorkspaceBuild("stop")
 export const deleteWorkspace = postWorkspaceBuild("delete")
 
+export const cancelWorkspaceBuild = async (workspaceBuildId: TypesGen.WorkspaceBuild["id"]): Promise<Types.Message> => {
+  const response = await axios.patch(`/api/v2/workspacebuilds/${workspaceBuildId}/cancel`)
+  return response.data
+}
+
 export const createUser = async (user: TypesGen.CreateUserRequest): Promise<TypesGen.User> => {
   const response = await axios.post<TypesGen.User>("/api/v2/users", user)
   return response.data
diff --git a/site/src/api/types.ts b/site/src/api/types.ts
index 5ea8d8ff86285..daf4e451ac5e8 100644
--- a/site/src/api/types.ts
+++ b/site/src/api/types.ts
@@ -12,3 +12,5 @@ export interface ReconnectingPTYRequest {
 }
 
 export type WorkspaceBuildTransition = "start" | "stop" | "delete"
+
+export type Message = { message: string }
diff --git a/site/src/components/Workspace/Workspace.stories.tsx b/site/src/components/Workspace/Workspace.stories.tsx
index d5087ebf949cd..44a26919588cb 100644
--- a/site/src/components/Workspace/Workspace.stories.tsx
+++ b/site/src/components/Workspace/Workspace.stories.tsx
@@ -31,7 +31,6 @@ Started.args = {
   workspace: MockWorkspace,
   handleStart: action("start"),
   handleStop: action("stop"),
-  handleRetry: action("retry"),
   resources: [MockWorkspaceResource, MockWorkspaceResource2],
   builds: [MockWorkspaceBuild],
 }
diff --git a/site/src/components/Workspace/Workspace.tsx b/site/src/components/Workspace/Workspace.tsx
index d773d1ee874eb..1194d024acb48 100644
--- a/site/src/components/Workspace/Workspace.tsx
+++ b/site/src/components/Workspace/Workspace.tsx
@@ -14,8 +14,8 @@ import { WorkspaceStats } from "../WorkspaceStats/WorkspaceStats"
 export interface WorkspaceProps {
   handleStart: () => void
   handleStop: () => void
-  handleRetry: () => void
   handleUpdate: () => void
+  handleCancel: () => void
   workspace: TypesGen.Workspace
   resources?: TypesGen.WorkspaceResource[]
   getResourcesError?: Error
@@ -28,8 +28,8 @@ export interface WorkspaceProps {
 export const Workspace: React.FC<WorkspaceProps> = ({
   handleStart,
   handleStop,
-  handleRetry,
   handleUpdate,
+  handleCancel,
   workspace,
   resources,
   getResourcesError,
@@ -55,8 +55,8 @@ export const Workspace: React.FC<WorkspaceProps> = ({
             workspace={workspace}
             handleStart={handleStart}
             handleStop={handleStop}
-            handleRetry={handleRetry}
             handleUpdate={handleUpdate}
+            handleCancel={handleCancel}
           />
         </div>
       </div>
diff --git a/site/src/components/WorkspaceActionButton/WorkspaceActionButton.stories.tsx b/site/src/components/WorkspaceActionButton/WorkspaceActionButton.stories.tsx
index 0a3b9b315a83e..4995769fabe4a 100644
--- a/site/src/components/WorkspaceActionButton/WorkspaceActionButton.stories.tsx
+++ b/site/src/components/WorkspaceActionButton/WorkspaceActionButton.stories.tsx
@@ -14,14 +14,4 @@ export const Example = Template.bind({})
 Example.args = {
   icon: <PlayArrowRoundedIcon />,
   label: "Start workspace",
-  loadingLabel: "Starting workspace",
-  isLoading: false,
-}
-
-export const Loading = Template.bind({})
-Loading.args = {
-  icon: <PlayArrowRoundedIcon />,
-  label: "Start workspace",
-  loadingLabel: "Starting workspace",
-  isLoading: true,
 }
diff --git a/site/src/components/WorkspaceActionButton/WorkspaceActionButton.tsx b/site/src/components/WorkspaceActionButton/WorkspaceActionButton.tsx
index 1188dec6a771c..631cff5f9bf4a 100644
--- a/site/src/components/WorkspaceActionButton/WorkspaceActionButton.tsx
+++ b/site/src/components/WorkspaceActionButton/WorkspaceActionButton.tsx
@@ -1,42 +1,17 @@
 import Button from "@material-ui/core/Button"
-import CircularProgress from "@material-ui/core/CircularProgress"
-import { makeStyles } from "@material-ui/core/styles"
 import React from "react"
 
 export interface WorkspaceActionButtonProps {
   label: string
-  loadingLabel: string
-  isLoading: boolean
   icon: JSX.Element
   onClick: () => void
   className?: string
 }
 
-export const WorkspaceActionButton: React.FC<WorkspaceActionButtonProps> = ({
-  label,
-  loadingLabel,
-  isLoading,
-  icon,
-  onClick,
-  className,
-}) => {
-  const styles = useStyles()
-
+export const WorkspaceActionButton: React.FC<WorkspaceActionButtonProps> = ({ label, icon, onClick, className }) => {
   return (
-    <Button
-      className={className}
-      startIcon={isLoading ? <CircularProgress size={12} className={styles.spinner} /> : icon}
-      onClick={onClick}
-      disabled={isLoading}
-    >
-      {isLoading ? loadingLabel : label}
+    <Button className={className} startIcon={icon} onClick={onClick}>
+      {label}
     </Button>
   )
 }
-
-const useStyles = makeStyles((theme) => ({
-  spinner: {
-    color: theme.palette.text.disabled,
-    marginRight: theme.spacing(1),
-  },
-}))
diff --git a/site/src/components/WorkspaceActions/WorkspaceActions.tsx b/site/src/components/WorkspaceActions/WorkspaceActions.tsx
index 15d0d391297a0..23f179107d55a 100644
--- a/site/src/components/WorkspaceActions/WorkspaceActions.tsx
+++ b/site/src/components/WorkspaceActions/WorkspaceActions.tsx
@@ -1,9 +1,9 @@
 import Button from "@material-ui/core/Button"
 import Link from "@material-ui/core/Link"
 import { makeStyles } from "@material-ui/core/styles"
+import CancelIcon from "@material-ui/icons/Cancel"
 import CloudDownloadIcon from "@material-ui/icons/CloudDownload"
 import PlayArrowRoundedIcon from "@material-ui/icons/PlayArrowRounded"
-import ReplayIcon from "@material-ui/icons/Replay"
 import StopIcon from "@material-ui/icons/Stop"
 import React from "react"
 import { Link as RouterLink } from "react-router-dom"
@@ -17,7 +17,7 @@ export const Language = {
   stopping: "Stopping workspace",
   start: "Start workspace",
   starting: "Starting workspace",
-  retry: "Retry",
+  cancel: "Cancel action",
   update: "Update workspace",
 }
 
@@ -28,20 +28,32 @@ export const Language = {
 const canAcceptJobs = (workspaceStatus: WorkspaceStatus) =>
   ["started", "stopped", "deleted", "error", "canceled"].includes(workspaceStatus)
 
+/**
+ *  Jobs that are in progress (queued or pending) can be canceled.
+ * @param workspaceStatus WorkspaceStatus
+ * @returns boolean
+ */
+const canCancelJobs = (workspaceStatus: WorkspaceStatus) =>
+  ["starting", "stopping", "deleting"].includes(workspaceStatus)
+
+const canStart = (workspaceStatus: WorkspaceStatus) => ["stopped", "canceled", "error"].includes(workspaceStatus)
+
+const canStop = (workspaceStatus: WorkspaceStatus) => ["started", "canceled", "error"].includes(workspaceStatus)
+
 export interface WorkspaceActionsProps {
   workspace: Workspace
   handleStart: () => void
   handleStop: () => void
-  handleRetry: () => void
   handleUpdate: () => void
+  handleCancel: () => void
 }
 
 export const WorkspaceActions: React.FC<WorkspaceActionsProps> = ({
   workspace,
   handleStart,
   handleStop,
-  handleRetry,
   handleUpdate,
+  handleCancel,
 }) => {
   const styles = useStyles()
   const workspaceStatus = getWorkspaceStatus(workspace.latest_build)
@@ -51,31 +63,30 @@ export const WorkspaceActions: React.FC<WorkspaceActionsProps> = ({
       <Link underline="none" component={RouterLink} to="edit">
         <Button variant="outlined">Settings</Button>
       </Link>
-      {(workspaceStatus === "started" || workspaceStatus === "stopping") && (
+      {canStart(workspaceStatus) && (
+        <WorkspaceActionButton
+          className={styles.actionButton}
+          icon={<PlayArrowRoundedIcon />}
+          onClick={handleStart}
+          label={Language.start}
+        />
+      )}
+      {canStop(workspaceStatus) && (
         <WorkspaceActionButton
           className={styles.actionButton}
           icon={<StopIcon />}
           onClick={handleStop}
           label={Language.stop}
-          loadingLabel={Language.stopping}
-          isLoading={workspaceStatus === "stopping"}
         />
       )}
-      {(workspaceStatus === "stopped" || workspaceStatus === "starting") && (
+      {canCancelJobs(workspaceStatus) && (
         <WorkspaceActionButton
           className={styles.actionButton}
-          icon={<PlayArrowRoundedIcon />}
-          onClick={handleStart}
-          label={Language.start}
-          loadingLabel={Language.starting}
-          isLoading={workspaceStatus === "starting"}
+          icon={<CancelIcon />}
+          onClick={handleCancel}
+          label={Language.cancel}
         />
       )}
-      {workspaceStatus === "error" && (
-        <Button className={styles.actionButton} startIcon={<ReplayIcon />} onClick={handleRetry}>
-          {Language.retry}
-        </Button>
-      )}
       {workspace.outdated && canAcceptJobs(workspaceStatus) && (
         <Button className={styles.actionButton} startIcon={<CloudDownloadIcon />} onClick={handleUpdate}>
           {Language.update}
@@ -89,6 +100,6 @@ const useStyles = makeStyles((theme) => ({
   actionButton: {
     // Set fixed width for the action buttons so they will not change the size
     // during the transitions
-    width: theme.spacing(30),
+    width: theme.spacing(27),
   },
 }))
diff --git a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
index c0f3bab812104..5340005dc1e07 100644
--- a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
+++ b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
@@ -6,6 +6,7 @@ import { Workspace } from "../../api/typesGenerated"
 import { Language } from "../../components/WorkspaceActions/WorkspaceActions"
 import {
   MockBuilds,
+  MockCanceledWorkspace,
   MockCancelingWorkspace,
   MockDeletedWorkspace,
   MockDeletingWorkspace,
@@ -86,45 +87,16 @@ describe("Workspace Page", () => {
       .mockImplementation(() => Promise.resolve(MockWorkspaceBuild))
     await testButton(Language.start, startWorkspaceMock)
   })
-  it("requests a start job when the user presses Retry after trying to start", async () => {
-    // Use a workspace that failed during start
+  it("requests cancellation when the user presses Cancel", async () => {
     server.use(
       rest.get(`/api/v2/workspaces/${MockWorkspace.id}`, (req, res, ctx) => {
-        return res(
-          ctx.status(200),
-          ctx.json({
-            ...MockFailedWorkspace,
-            latest_build: {
-              ...MockFailedWorkspace.latest_build,
-              transition: "start",
-            },
-          }),
-        )
+        return res(ctx.status(200), ctx.json(MockStartingWorkspace))
       }),
     )
-    const startWorkSpaceMock = jest.spyOn(api, "startWorkspace").mockResolvedValueOnce(MockWorkspaceBuild)
-    await testButton(Language.retry, startWorkSpaceMock)
-  })
-  it("requests a stop job when the user presses Retry after trying to stop", async () => {
-    // Use a workspace that failed during stop
-    server.use(
-      rest.get(`/api/v2/workspaces/${MockWorkspace.id}`, (req, res, ctx) => {
-        return res(
-          ctx.status(200),
-          ctx.json({
-            ...MockFailedWorkspace,
-            latest_build: {
-              ...MockFailedWorkspace.latest_build,
-              transition: "stop",
-            },
-          }),
-        )
-      }),
-    )
-    const stopWorkspaceMock = jest
-      .spyOn(api, "stopWorkspace")
-      .mockImplementation(() => Promise.resolve(MockWorkspaceBuild))
-    await testButton(Language.retry, stopWorkspaceMock)
+    const cancelWorkspaceMock = jest
+      .spyOn(api, "cancelWorkspaceBuild")
+      .mockImplementation(() => Promise.resolve({ message: "job canceled" }))
+    await testButton(Language.cancel, cancelWorkspaceMock)
   })
   it("requests a template when the user presses Update", async () => {
     const getTemplateMock = jest.spyOn(api, "getTemplate").mockResolvedValueOnce(MockTemplate)
@@ -153,6 +125,9 @@ describe("Workspace Page", () => {
   it("shows the Canceling status when the workspace is canceling", async () => {
     await testStatus(MockCancelingWorkspace, DisplayStatusLanguage.canceling)
   })
+  it("shows the Canceled status when the workspace is canceling", async () => {
+    await testStatus(MockCanceledWorkspace, DisplayStatusLanguage.canceled)
+  })
   it("shows the Deleting status when the workspace is deleting", async () => {
     await testStatus(MockDeletingWorkspace, DisplayStatusLanguage.deleting)
   })
diff --git a/site/src/pages/WorkspacePage/WorkspacePage.tsx b/site/src/pages/WorkspacePage/WorkspacePage.tsx
index fb3556019aca7..dcb0068d4301c 100644
--- a/site/src/pages/WorkspacePage/WorkspacePage.tsx
+++ b/site/src/pages/WorkspacePage/WorkspacePage.tsx
@@ -36,8 +36,8 @@ export const WorkspacePage: React.FC = () => {
             workspace={workspace}
             handleStart={() => workspaceSend("START")}
             handleStop={() => workspaceSend("STOP")}
-            handleRetry={() => workspaceSend("RETRY")}
             handleUpdate={() => workspaceSend("UPDATE")}
+            handleCancel={() => workspaceSend("CANCEL")}
             resources={resources}
             getResourcesError={getResourcesError instanceof Error ? getResourcesError : undefined}
             builds={builds}
diff --git a/site/src/testHelpers/entities.ts b/site/src/testHelpers/entities.ts
index 06bd8201c414e..c2b68ee72c43a 100644
--- a/site/src/testHelpers/entities.ts
+++ b/site/src/testHelpers/entities.ts
@@ -182,7 +182,7 @@ export const MockDeletingWorkspace: TypesGen.Workspace = {
 }
 export const MockDeletedWorkspace: TypesGen.Workspace = { ...MockWorkspace, latest_build: MockWorkspaceBuildDelete }
 
-export const MockOutdatedWorkspace: TypesGen.Workspace = { ...MockWorkspace, outdated: true }
+export const MockOutdatedWorkspace: TypesGen.Workspace = { ...MockFailedWorkspace, outdated: true }
 
 export const MockWorkspaceAgent: TypesGen.WorkspaceAgent = {
   architecture: "amd64",
@@ -506,3 +506,7 @@ export const MockWorkspaceBuildLogs: TypesGen.ProvisionerJobLog[] = [
     output: "",
   },
 ]
+
+export const MockCancellationMessage = {
+  message: "Job successfully canceled",
+}
diff --git a/site/src/testHelpers/handlers.ts b/site/src/testHelpers/handlers.ts
index 1870e7b4bfbdf..d5bc8c5dbc7d7 100644
--- a/site/src/testHelpers/handlers.ts
+++ b/site/src/testHelpers/handlers.ts
@@ -130,4 +130,7 @@ export const handlers = [
   rest.get("/api/v2/workspacebuilds/:workspaceBuildId/logs", (req, res, ctx) => {
     return res(ctx.status(200), ctx.json(M.MockWorkspaceBuildLogs))
   }),
+  rest.patch("/api/v2/workspacebuilds/:workspaceBuildId/cancel", (req, res, ctx) => {
+    return res(ctx.status(200), ctx.json(M.MockCancellationMessage))
+  }),
 ]
diff --git a/site/src/util/workspace.ts b/site/src/util/workspace.ts
index b78b4b716b7c3..b176b9de965be 100644
--- a/site/src/util/workspace.ts
+++ b/site/src/util/workspace.ts
@@ -58,8 +58,8 @@ export const DisplayStatusLanguage = {
   stopped: "Stopped",
   deleting: "Deleting",
   deleted: "Deleted",
-  canceling: "Canceling",
-  canceled: "Canceled",
+  canceling: "Canceling action",
+  canceled: "Canceled action",
   failed: "Failed",
   queued: "Queued",
 }
diff --git a/site/src/xServices/workspace/workspaceXService.ts b/site/src/xServices/workspace/workspaceXService.ts
index f61ca29c9e4ca..075475b45a9d0 100644
--- a/site/src/xServices/workspace/workspaceXService.ts
+++ b/site/src/xServices/workspace/workspaceXService.ts
@@ -1,6 +1,7 @@
 import { assign, createMachine, send } from "xstate"
 import { pure } from "xstate/lib/actions"
 import * as API from "../../api/api"
+import * as Types from "../../api/types"
 import * as TypesGen from "../../api/typesGenerated"
 import { displayError } from "../../components/GlobalSnackbar/utils"
 
@@ -32,14 +33,15 @@ export interface WorkspaceContext {
   builds?: TypesGen.WorkspaceBuild[]
   getBuildsError?: Error | unknown
   loadMoreBuildsError?: Error | unknown
+  cancellationMessage: string
 }
 
 export type WorkspaceEvent =
   | { type: "GET_WORKSPACE"; workspaceId: string }
   | { type: "START" }
   | { type: "STOP" }
-  | { type: "RETRY" }
   | { type: "UPDATE" }
+  | { type: "CANCEL" }
   | { type: "LOAD_MORE_BUILDS" }
   | { type: "REFRESH_TIMELINE" }
 
@@ -62,6 +64,9 @@ export const workspaceMachine = createMachine(
         stopWorkspace: {
           data: TypesGen.WorkspaceBuild
         }
+        cancelWorkspace: {
+          data: Types.Message
+        }
         refreshWorkspace: {
           data: TypesGen.Workspace | undefined
         }
@@ -131,8 +136,8 @@ export const workspaceMachine = createMachine(
                 on: {
                   START: "requestingStart",
                   STOP: "requestingStop",
-                  RETRY: [{ cond: "triedToStart", target: "requestingStart" }, { target: "requestingStop" }],
                   UPDATE: "refreshingTemplate",
+                  CANCEL: "requestingCancel",
                 },
               },
               requestingStart: {
@@ -165,6 +170,21 @@ export const workspaceMachine = createMachine(
                   },
                 },
               },
+              requestingCancel: {
+                entry: "clearCancellationMessage",
+                invoke: {
+                  id: "cancelWorkspace",
+                  src: "cancelWorkspace",
+                  onDone: {
+                    target: "idle",
+                    actions: ["assignCancellationMessage", "refreshTimeline"],
+                  },
+                  onError: {
+                    target: "idle",
+                    actions: ["assignCancellationMessage", "displayCancellationError"],
+                  },
+                },
+              },
               refreshingTemplate: {
                 entry: "clearRefreshTemplateError",
                 invoke: {
@@ -293,6 +313,17 @@ export const workspaceMachine = createMachine(
         assign({
           buildError: undefined,
         }),
+      assignCancellationMessage: (_, event) =>
+        assign({
+          cancellationMessage: event.data,
+        }),
+      clearCancellationMessage: (_) =>
+        assign({
+          cancellationMessage: undefined,
+        }),
+      displayCancellationError: (context) => {
+        displayError(context.cancellationMessage)
+      },
       assignRefreshWorkspaceError: (_, event) =>
         assign({
           refreshWorkspaceError: event.data,
@@ -312,6 +343,7 @@ export const workspaceMachine = createMachine(
         assign({
           refreshTemplateError: undefined,
         }),
+      // Resources
       assignResources: assign({
         resources: (_, event) => event.data,
       }),
@@ -369,7 +401,6 @@ export const workspaceMachine = createMachine(
       }),
     },
     guards: {
-      triedToStart: (context) => context.workspace?.latest_build.transition === "start",
       hasMoreBuilds: (_) => false,
     },
     services: {
@@ -397,6 +428,13 @@ export const workspaceMachine = createMachine(
           throw Error("Cannot stop workspace without workspace id")
         }
       },
+      cancelWorkspace: async (context) => {
+        if (context.workspace) {
+          return await API.cancelWorkspaceBuild(context.workspace.latest_build.id)
+        } else {
+          throw Error("Cannot cancel workspace without build id")
+        }
+      },
       refreshWorkspace: async (context) => {
         if (context.workspace) {
           return await API.getWorkspace(context.workspace.id)