diff --git a/site/src/components/LoadingButton/LoadingButton.tsx b/site/src/components/LoadingButton/LoadingButton.tsx
index 9f8aaa3d592a7..0e4e51bfbc6a8 100644
--- a/site/src/components/LoadingButton/LoadingButton.tsx
+++ b/site/src/components/LoadingButton/LoadingButton.tsx
@@ -1,11 +1,14 @@
 import Button, { ButtonProps } from "@material-ui/core/Button"
 import CircularProgress from "@material-ui/core/CircularProgress"
 import { makeStyles } from "@material-ui/core/styles"
-import * as React from "react"
+import { Theme } from "@material-ui/core/styles/createMuiTheme"
+import { FC } from "react"
 
 export interface LoadingButtonProps extends ButtonProps {
   /** Whether or not to disable the button and show a spinner */
   loading?: boolean
+  /** An optional label to display with the loading spinner */
+  loadingLabel?: string
 }
 
 /**
@@ -14,12 +17,13 @@ export interface LoadingButtonProps extends ButtonProps {
  * In Material-UI 5+ - this is built-in, but since we're on an earlier version,
  * we have to roll our own.
  */
-export const LoadingButton: React.FC<LoadingButtonProps> = ({
+export const LoadingButton: FC<LoadingButtonProps> = ({
   loading = false,
+  loadingLabel,
   children,
   ...rest
 }) => {
-  const styles = useStyles()
+  const styles = useStyles({ hasLoadingLabel: !!loadingLabel })
   const hidden = loading ? { opacity: 0 } : undefined
 
   return (
@@ -30,17 +34,35 @@ export const LoadingButton: React.FC<LoadingButtonProps> = ({
           <CircularProgress size={18} className={styles.spinner} />
         </div>
       )}
+      {!!loadingLabel && loadingLabel}
     </Button>
   )
 }
 
-const useStyles = makeStyles((theme) => ({
+interface StyleProps {
+  hasLoadingLabel?: boolean
+}
+
+const useStyles = makeStyles<Theme, StyleProps>((theme) => ({
   loader: {
-    position: "absolute",
+    position: (props) => {
+      if (!props.hasLoadingLabel) {
+        return "absolute"
+      }
+    },
+    transform: (props) => {
+      if (!props.hasLoadingLabel) {
+        return "translate(-50%, -50%)"
+      }
+    },
+    marginRight: (props) => {
+      if (props.hasLoadingLabel) {
+        return "10px"
+      }
+    },
     top: "50%",
     left: "50%",
-    transform: "translate(-50%, -50%)",
-    height: 18,
+    height: 22, // centering loading icon
     width: 18,
   },
   spinner: {
diff --git a/site/src/components/WorkspaceActionButton/WorkspaceActionButton.tsx b/site/src/components/WorkspaceActionButton/WorkspaceActionButton.tsx
index 89fec93dccf99..212da090b7e52 100644
--- a/site/src/components/WorkspaceActionButton/WorkspaceActionButton.tsx
+++ b/site/src/components/WorkspaceActionButton/WorkspaceActionButton.tsx
@@ -2,10 +2,11 @@ import Button from "@material-ui/core/Button"
 import { FC } from "react"
 
 export interface WorkspaceActionButtonProps {
-  label: string
+  label?: string
   icon: JSX.Element
   onClick: () => void
   className?: string
+  ariaLabel?: string
 }
 
 export const WorkspaceActionButton: FC<WorkspaceActionButtonProps> = ({
@@ -13,10 +14,11 @@ export const WorkspaceActionButton: FC<WorkspaceActionButtonProps> = ({
   icon,
   onClick,
   className,
+  ariaLabel,
 }) => {
   return (
-    <Button className={className} startIcon={icon} onClick={onClick}>
-      {label}
+    <Button className={className} startIcon={icon} onClick={onClick} aria-label={ariaLabel}>
+      {!!label && label}
     </Button>
   )
 }
diff --git a/site/src/components/WorkspaceActions/ActionCtas.tsx b/site/src/components/WorkspaceActions/ActionCtas.tsx
index 1cf762ad42096..2240701c47db4 100644
--- a/site/src/components/WorkspaceActions/ActionCtas.tsx
+++ b/site/src/components/WorkspaceActions/ActionCtas.tsx
@@ -1,12 +1,15 @@
 import Button from "@material-ui/core/Button"
 import { makeStyles } from "@material-ui/core/styles"
+import BlockIcon from "@material-ui/icons/Block"
 import CloudQueueIcon from "@material-ui/icons/CloudQueue"
 import CropSquareIcon from "@material-ui/icons/CropSquare"
 import DeleteOutlineIcon from "@material-ui/icons/DeleteOutline"
-import HighlightOffIcon from "@material-ui/icons/HighlightOff"
 import PlayCircleOutlineIcon from "@material-ui/icons/PlayCircleOutline"
+import { LoadingButton } from "components/LoadingButton/LoadingButton"
 import { FC } from "react"
+import { combineClasses } from "util/combineClasses"
 import { WorkspaceActionButton } from "../WorkspaceActionButton/WorkspaceActionButton"
+import { WorkspaceStateEnum } from "./constants"
 
 export const Language = {
   start: "Start",
@@ -14,6 +17,10 @@ export const Language = {
   delete: "Delete",
   cancel: "Cancel",
   update: "Update",
+  // these labels are used in WorkspaceActions.tsx
+  starting: "Starting...",
+  stopping: "Stopping...",
+  deleting: "Deleting...",
 }
 
 interface WorkspaceAction {
@@ -72,12 +79,42 @@ export const DeleteButton: FC<WorkspaceAction> = ({ handleAction }) => {
 export const CancelButton: FC<WorkspaceAction> = ({ handleAction }) => {
   const styles = useStyles()
 
+  // this is an icon button, so it's important to include an aria label
   return (
     <WorkspaceActionButton
-      className={styles.actionButton}
-      icon={<HighlightOffIcon />}
+      icon={<BlockIcon />}
       onClick={handleAction}
-      label={Language.cancel}
+      className={styles.cancelButton}
+      ariaLabel="cancel action"
+    />
+  )
+}
+
+interface DisabledProps {
+  workspaceState: WorkspaceStateEnum
+}
+
+export const DisabledButton: FC<DisabledProps> = ({ workspaceState }) => {
+  const styles = useStyles()
+
+  return (
+    <Button disabled className={styles.actionButton}>
+      {workspaceState}
+    </Button>
+  )
+}
+
+interface LoadingProps {
+  label: string
+}
+
+export const ActionLoadingButton: FC<LoadingProps> = ({ label }) => {
+  const styles = useStyles()
+  return (
+    <LoadingButton
+      loading
+      loadingLabel={label}
+      className={combineClasses([styles.loadingButton, styles.actionButton])}
     />
   )
 }
@@ -86,8 +123,26 @@ 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(16),
+    width: theme.spacing(20),
     border: "none",
     borderRadius: `${theme.shape.borderRadius}px 0px 0px ${theme.shape.borderRadius}px`,
   },
+  cancelButton: {
+    "&.MuiButton-root": {
+      padding: "0px 0px !important",
+      border: "none",
+      borderLeft: `1px solid ${theme.palette.divider}`,
+      borderRadius: `0px ${theme.shape.borderRadius}px ${theme.shape.borderRadius}px 0px`,
+      width: "63px", // matching dropdown button so button grouping doesn't grow in size
+    },
+    "& .MuiButton-label": {
+      marginLeft: "10px",
+    },
+  },
+  // 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",
+  },
 }))
diff --git a/site/src/components/WorkspaceActions/DropdownContent/DropdownContent.stories.tsx b/site/src/components/WorkspaceActions/DropdownContent/DropdownContent.stories.tsx
new file mode 100644
index 0000000000000..edde3acabdb64
--- /dev/null
+++ b/site/src/components/WorkspaceActions/DropdownContent/DropdownContent.stories.tsx
@@ -0,0 +1,54 @@
+import { Story } from "@storybook/react"
+import { DeleteButton, StartButton, StopButton } from "../ActionCtas"
+import {
+  ButtonMapping,
+  ButtonTypesEnum,
+  WorkspaceStateActions,
+  WorkspaceStateEnum,
+} from "../constants"
+import { DropdownContent, DropdownContentProps } from "./DropdownContent"
+
+// These are the stories for the secondary actions (housed in the dropdown)
+// in WorkspaceActions.tsx
+
+export default {
+  title: "WorkspaceActionsDropdown",
+  component: DropdownContent,
+}
+
+const Template: Story<DropdownContentProps> = (args) => <DropdownContent {...args} />
+
+const buttonMappingMock: Partial<ButtonMapping> = {
+  [ButtonTypesEnum.delete]: <DeleteButton handleAction={() => jest.fn()} />,
+  [ButtonTypesEnum.start]: <StartButton handleAction={() => jest.fn()} />,
+  [ButtonTypesEnum.stop]: <StopButton handleAction={() => jest.fn()} />,
+  [ButtonTypesEnum.delete]: <DeleteButton handleAction={() => jest.fn()} />,
+}
+
+const defaultArgs = {
+  buttonMapping: buttonMappingMock,
+}
+
+export const Started = Template.bind({})
+Started.args = {
+  ...defaultArgs,
+  secondaryActions: WorkspaceStateActions[WorkspaceStateEnum.started].secondary,
+}
+
+export const Stopped = Template.bind({})
+Stopped.args = {
+  ...defaultArgs,
+  secondaryActions: WorkspaceStateActions[WorkspaceStateEnum.stopped].secondary,
+}
+
+export const Canceled = Template.bind({})
+Canceled.args = {
+  ...defaultArgs,
+  secondaryActions: WorkspaceStateActions[WorkspaceStateEnum.canceled].secondary,
+}
+
+export const Errored = Template.bind({})
+Errored.args = {
+  ...defaultArgs,
+  secondaryActions: WorkspaceStateActions[WorkspaceStateEnum.error].secondary,
+}
diff --git a/site/src/components/WorkspaceActions/DropdownContent/DropdownContent.tsx b/site/src/components/WorkspaceActions/DropdownContent/DropdownContent.tsx
new file mode 100644
index 0000000000000..f4da8f13eb6ad
--- /dev/null
+++ b/site/src/components/WorkspaceActions/DropdownContent/DropdownContent.tsx
@@ -0,0 +1,33 @@
+import { makeStyles } from "@material-ui/core/styles"
+import { FC } from "react"
+import { ButtonMapping, ButtonTypesEnum } from "../constants"
+
+export interface DropdownContentProps {
+  secondaryActions: ButtonTypesEnum[]
+  buttonMapping: Partial<ButtonMapping>
+}
+
+/* secondary workspace CTAs */
+export const DropdownContent: FC<DropdownContentProps> = ({ secondaryActions, buttonMapping }) => {
+  const styles = useStyles()
+
+  return (
+    <span data-testid="secondary-ctas">
+      {secondaryActions.map((action) => (
+        <div key={action} className={styles.popoverActionButton}>
+          {buttonMapping[action]}
+        </div>
+      ))}
+    </span>
+  )
+}
+
+const useStyles = makeStyles(() => ({
+  popoverActionButton: {
+    "& .MuiButtonBase-root": {
+      backgroundColor: "unset",
+      justifyContent: "start",
+      padding: "0px",
+    },
+  },
+}))
diff --git a/site/src/components/WorkspaceActions/WorkspaceActions.test.tsx b/site/src/components/WorkspaceActions/WorkspaceActions.test.tsx
index ca8b84d0e2d68..81d29c7222ec3 100644
--- a/site/src/components/WorkspaceActions/WorkspaceActions.test.tsx
+++ b/site/src/components/WorkspaceActions/WorkspaceActions.test.tsx
@@ -5,6 +5,19 @@ import { Language } from "./ActionCtas"
 import { WorkspaceStateEnum } from "./constants"
 import { WorkspaceActions, WorkspaceActionsProps } from "./WorkspaceActions"
 
+const renderComponent = async (props: Partial<WorkspaceActionsProps> = {}) => {
+  render(
+    <WorkspaceActions
+      workspace={props.workspace ?? Mocks.MockWorkspace}
+      handleStart={jest.fn()}
+      handleStop={jest.fn()}
+      handleDelete={jest.fn()}
+      handleUpdate={jest.fn()}
+      handleCancel={jest.fn()}
+    />,
+  )
+}
+
 const renderAndClick = async (props: Partial<WorkspaceActionsProps> = {}) => {
   render(
     <WorkspaceActions
@@ -22,9 +35,14 @@ const renderAndClick = async (props: Partial<WorkspaceActionsProps> = {}) => {
 
 describe("WorkspaceActions", () => {
   describe("when the workspace is starting", () => {
-    it("primary is cancel; no secondary", async () => {
-      await renderAndClick({ workspace: Mocks.MockStartingWorkspace })
-      expect(screen.getByTestId("primary-cta")).toHaveTextContent(Language.cancel)
+    it("primary is starting; cancel is available; no secondary", async () => {
+      await renderComponent({ workspace: Mocks.MockStartingWorkspace })
+      expect(screen.getByTestId("primary-cta")).toHaveTextContent(Language.starting)
+      expect(
+        screen.getByRole("button", {
+          name: "cancel action",
+        }),
+      ).toBeInTheDocument()
       expect(screen.queryByTestId("secondary-ctas")).toBeNull()
     })
   })
@@ -36,9 +54,14 @@ describe("WorkspaceActions", () => {
     })
   })
   describe("when the workspace is stopping", () => {
-    it("primary is cancel; no secondary", async () => {
-      await renderAndClick({ workspace: Mocks.MockStoppingWorkspace })
-      expect(screen.getByTestId("primary-cta")).toHaveTextContent(Language.cancel)
+    it("primary is stopping; cancel is available; no secondary", async () => {
+      await renderComponent({ workspace: Mocks.MockStoppingWorkspace })
+      expect(screen.getByTestId("primary-cta")).toHaveTextContent(Language.stopping)
+      expect(
+        screen.getByRole("button", {
+          name: "cancel action",
+        }),
+      ).toBeInTheDocument()
       expect(screen.queryByTestId("secondary-ctas")).toBeNull()
     })
   })
@@ -65,9 +88,14 @@ describe("WorkspaceActions", () => {
     })
   })
   describe("when the workspace is deleting", () => {
-    it("primary is cancel; no secondary", async () => {
-      await renderAndClick({ workspace: Mocks.MockDeletingWorkspace })
-      expect(screen.getByTestId("primary-cta")).toHaveTextContent(Language.cancel)
+    it("primary is deleting; cancel is available; no secondary", async () => {
+      await renderComponent({ workspace: Mocks.MockDeletingWorkspace })
+      expect(screen.getByTestId("primary-cta")).toHaveTextContent(Language.deleting)
+      expect(
+        screen.getByRole("button", {
+          name: "cancel action",
+        }),
+      ).toBeInTheDocument()
       expect(screen.queryByTestId("secondary-ctas")).toBeNull()
     })
   })
diff --git a/site/src/components/WorkspaceActions/WorkspaceActions.tsx b/site/src/components/WorkspaceActions/WorkspaceActions.tsx
index cfb4c5be47d6f..e4c2339194f8e 100644
--- a/site/src/components/WorkspaceActions/WorkspaceActions.tsx
+++ b/site/src/components/WorkspaceActions/WorkspaceActions.tsx
@@ -1,12 +1,27 @@
 import Button from "@material-ui/core/Button"
 import Popover from "@material-ui/core/Popover"
 import { makeStyles } from "@material-ui/core/styles"
-import { FC, ReactNode, useEffect, useMemo, useRef, useState } from "react"
+import { FC, useEffect, useMemo, useRef, useState } from "react"
 import { Workspace } from "../../api/typesGenerated"
 import { getWorkspaceStatus, WorkspaceStatus } from "../../util/workspace"
 import { CloseDropdown, OpenDropdown } from "../DropdownArrows/DropdownArrows"
-import { CancelButton, DeleteButton, StartButton, StopButton, UpdateButton } from "./ActionCtas"
-import { ButtonTypesEnum, WorkspaceStateActions, WorkspaceStateEnum } from "./constants"
+import {
+  ActionLoadingButton,
+  CancelButton,
+  DeleteButton,
+  DisabledButton,
+  Language,
+  StartButton,
+  StopButton,
+  UpdateButton,
+} from "./ActionCtas"
+import {
+  ButtonMapping,
+  ButtonTypesEnum,
+  WorkspaceStateActions,
+  WorkspaceStateEnum,
+} from "./constants"
+import { DropdownContent } from "./DropdownContent/DropdownContent"
 
 /**
  * Jobs submitted while another job is in progress will be discarded,
@@ -69,74 +84,66 @@ export const WorkspaceActions: FC<WorkspaceActionsProps> = ({
     }
   }, [workspaceStatus])
 
-  const disabledButton = (
-    <Button disabled className={styles.actionButton}>
-      {workspaceState}
-    </Button>
-  )
-
-  type ButtonMapping = {
-    [key in ButtonTypesEnum]: ReactNode
-  }
-
   // A mapping of button type to the corresponding React component
   const buttonMapping: ButtonMapping = {
     [ButtonTypesEnum.update]: <UpdateButton handleAction={handleUpdate} />,
     [ButtonTypesEnum.start]: <StartButton handleAction={handleStart} />,
+    [ButtonTypesEnum.starting]: <ActionLoadingButton label={Language.starting} />,
     [ButtonTypesEnum.stop]: <StopButton handleAction={handleStop} />,
+    [ButtonTypesEnum.stopping]: <ActionLoadingButton label={Language.stopping} />,
     [ButtonTypesEnum.delete]: <DeleteButton handleAction={handleDelete} />,
+    [ButtonTypesEnum.deleting]: <ActionLoadingButton label={Language.deleting} />,
     [ButtonTypesEnum.cancel]: <CancelButton handleAction={handleCancel} />,
-    [ButtonTypesEnum.canceling]: disabledButton,
-    [ButtonTypesEnum.disabled]: disabledButton,
-    [ButtonTypesEnum.queued]: disabledButton,
-    [ButtonTypesEnum.error]: disabledButton,
-    [ButtonTypesEnum.loading]: disabledButton,
+    [ButtonTypesEnum.canceling]: <DisabledButton workspaceState={workspaceState} />,
+    [ButtonTypesEnum.disabled]: <DisabledButton workspaceState={workspaceState} />,
+    [ButtonTypesEnum.queued]: <DisabledButton workspaceState={workspaceState} />,
+    [ButtonTypesEnum.error]: <DisabledButton workspaceState={workspaceState} />,
+    [ButtonTypesEnum.loading]: <DisabledButton workspaceState={workspaceState} />,
   }
 
   return (
     <span className={styles.buttonContainer}>
       {/* primary workspace CTA */}
       <span data-testid="primary-cta">{buttonMapping[actions.primary]}</span>
-
-      {/* popover toggle button */}
-      <Button
-        data-testid="workspace-actions-button"
-        aria-controls="workspace-actions-menu"
-        aria-haspopup="true"
-        className={styles.dropdownButton}
-        ref={anchorRef}
-        disabled={!actions.secondary.length}
-        onClick={() => {
-          setIsOpen(true)
-        }}
-      >
-        {isOpen ? <CloseDropdown /> : <OpenDropdown />}
-      </Button>
-
-      <Popover
-        classes={{ paper: styles.popoverPaper }}
-        id={id}
-        open={isOpen}
-        anchorEl={anchorRef.current}
-        onClose={() => setIsOpen(false)}
-        anchorOrigin={{
-          vertical: "bottom",
-          horizontal: "right",
-        }}
-        transformOrigin={{
-          vertical: "top",
-          horizontal: "right",
-        }}
-      >
-        {/* secondary workspace CTAs */}
-        <span data-testid="secondary-ctas">
-          {actions.secondary.map((action) => (
-            <div key={action} className={styles.popoverActionButton}>
-              {buttonMapping[action]}
-            </div>
-          ))}
-        </span>
-      </Popover>
+      {actions.canCancel ? (
+        // cancel CTA
+        <>{buttonMapping[ButtonTypesEnum.cancel]}</>
+      ) : (
+        <>
+          {/* popover toggle button */}
+          <Button
+            data-testid="workspace-actions-button"
+            aria-controls="workspace-actions-menu"
+            aria-haspopup="true"
+            className={styles.dropdownButton}
+            ref={anchorRef}
+            disabled={!actions.secondary.length}
+            onClick={() => {
+              setIsOpen(true)
+            }}
+          >
+            {isOpen ? <CloseDropdown /> : <OpenDropdown />}
+          </Button>
+          <Popover
+            classes={{ paper: styles.popoverPaper }}
+            id={id}
+            open={isOpen}
+            anchorEl={anchorRef.current}
+            onClose={() => setIsOpen(false)}
+            anchorOrigin={{
+              vertical: "bottom",
+              horizontal: "right",
+            }}
+            transformOrigin={{
+              vertical: "top",
+              horizontal: "right",
+            }}
+          >
+            {/* secondary workspace CTAs */}
+            <DropdownContent secondaryActions={actions.secondary} buttonMapping={buttonMapping} />
+          </Popover>
+        </>
+      )}
     </span>
   )
 }
@@ -152,25 +159,11 @@ const useStyles = makeStyles((theme) => ({
     borderLeft: `1px solid ${theme.palette.divider}`,
     borderRadius: `0px ${theme.shape.borderRadius}px ${theme.shape.borderRadius}px 0px`,
     minWidth: "unset",
-    width: "35px",
+    width: "63px", // matching cancel button so button grouping doesn't grow in size
     "& .MuiButton-label": {
       marginRight: "8px",
     },
   },
-  actionButton: {
-    // Set fixed width for the action buttons so they will not change the size
-    // during the transitions
-    width: theme.spacing(16),
-    border: "none",
-    borderRadius: `${theme.shape.borderRadius}px 0px 0px ${theme.shape.borderRadius}px`,
-  },
-  popoverActionButton: {
-    "& .MuiButtonBase-root": {
-      backgroundColor: "unset",
-      justifyContent: "start",
-      padding: "0px",
-    },
-  },
   popoverPaper: {
     padding: `${theme.spacing(2)}px ${theme.spacing(3)}px ${theme.spacing(3)}px`,
   },
diff --git a/site/src/components/WorkspaceActions/constants.ts b/site/src/components/WorkspaceActions/constants.ts
index 38391b1ec6218..ecb7292a0d6ed 100644
--- a/site/src/components/WorkspaceActions/constants.ts
+++ b/site/src/components/WorkspaceActions/constants.ts
@@ -1,3 +1,5 @@
+import { ReactNode } from "react"
+
 // all the possible states returned by the API
 export enum WorkspaceStateEnum {
   starting = "Starting",
@@ -16,8 +18,11 @@ export enum WorkspaceStateEnum {
 // the button types we have
 export enum ButtonTypesEnum {
   start,
+  starting,
   stop,
+  stopping,
   delete,
+  deleting,
   update,
   cancel,
   error,
@@ -28,10 +33,15 @@ export enum ButtonTypesEnum {
   loading,
 }
 
+export type ButtonMapping = {
+  [key in ButtonTypesEnum]: ReactNode
+}
+
 type StateActionsType = {
   [key in WorkspaceStateEnum]: {
     primary: ButtonTypesEnum
     secondary: ButtonTypesEnum[]
+    canCancel: boolean
   }
 }
 
@@ -40,29 +50,35 @@ type StateActionsType = {
 // 'Secondary' actions are ctas housed within the popover
 export const WorkspaceStateActions: StateActionsType = {
   [WorkspaceStateEnum.starting]: {
-    primary: ButtonTypesEnum.cancel,
+    primary: ButtonTypesEnum.starting,
     secondary: [],
+    canCancel: true,
   },
   [WorkspaceStateEnum.started]: {
     primary: ButtonTypesEnum.stop,
     secondary: [ButtonTypesEnum.delete],
+    canCancel: false,
   },
   [WorkspaceStateEnum.stopping]: {
-    primary: ButtonTypesEnum.cancel,
+    primary: ButtonTypesEnum.stopping,
     secondary: [],
+    canCancel: true,
   },
   [WorkspaceStateEnum.stopped]: {
     primary: ButtonTypesEnum.start,
     secondary: [ButtonTypesEnum.delete],
+    canCancel: false,
   },
   [WorkspaceStateEnum.canceled]: {
     primary: ButtonTypesEnum.start,
     secondary: [ButtonTypesEnum.stop, ButtonTypesEnum.delete],
+    canCancel: false,
   },
   // in the case of an error
   [WorkspaceStateEnum.error]: {
     primary: ButtonTypesEnum.start, // give the user the ability to start a workspace again
     secondary: [ButtonTypesEnum.delete], // allows the user to delete
+    canCancel: false,
   },
   /**
    * disabled states
@@ -70,21 +86,26 @@ export const WorkspaceStateActions: StateActionsType = {
   [WorkspaceStateEnum.canceling]: {
     primary: ButtonTypesEnum.canceling,
     secondary: [],
+    canCancel: false,
   },
   [WorkspaceStateEnum.deleting]: {
-    primary: ButtonTypesEnum.cancel,
+    primary: ButtonTypesEnum.deleting,
     secondary: [],
+    canCancel: true,
   },
   [WorkspaceStateEnum.deleted]: {
     primary: ButtonTypesEnum.disabled,
     secondary: [],
+    canCancel: false,
   },
   [WorkspaceStateEnum.queued]: {
     primary: ButtonTypesEnum.queued,
     secondary: [],
+    canCancel: false,
   },
   [WorkspaceStateEnum.loading]: {
     primary: ButtonTypesEnum.loading,
     secondary: [],
+    canCancel: false,
   },
 }
diff --git a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
index 35b9d2243ac5e..25296de6001b3 100644
--- a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
+++ b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
@@ -43,9 +43,6 @@ const renderWorkspacePage = async () => {
 
 const testButton = async (label: string, actionMock: jest.SpyInstance) => {
   await renderWorkspacePage()
-  // open the workspace action popover so we have access to all available ctas
-  const trigger = await screen.findByTestId("workspace-actions-button")
-  trigger.click()
   // REMARK: exact here because the "Start" button and "START" label for
   //         workspace schedule could otherwise conflict.
   const button = await screen.findByText(label, { exact: true })
@@ -122,7 +119,15 @@ describe("Workspace Page", () => {
     const cancelWorkspaceMock = jest
       .spyOn(api, "cancelWorkspaceBuild")
       .mockImplementation(() => Promise.resolve({ message: "job canceled" }))
-    await testButton(Language.cancel, cancelWorkspaceMock)
+
+    await renderWorkspacePage()
+
+    const cancelButton = await screen.findByRole("button", {
+      name: "cancel action",
+    })
+    await waitFor(() => fireEvent.click(cancelButton))
+
+    expect(cancelWorkspaceMock).toBeCalled()
   })
   it("requests a template when the user presses Update", async () => {
     const getTemplateMock = jest.spyOn(api, "getTemplate").mockResolvedValueOnce(MockTemplate)