diff --git a/site/src/components/Workspace/Workspace.tsx b/site/src/components/Workspace/Workspace.tsx
index a9849063b6034..145858f6e24f2 100644
--- a/site/src/components/Workspace/Workspace.tsx
+++ b/site/src/components/Workspace/Workspace.tsx
@@ -34,10 +34,12 @@ export interface WorkspaceProps {
     onExtend: () => void
   }
   scheduleProps: {
-    onDeadlinePlus: () => void
-    onDeadlineMinus: () => void
+    onDeadlinePlus: (hours: number) => void
+    onDeadlineMinus: (hours: number) => void
     deadlinePlusEnabled: () => boolean
     deadlineMinusEnabled: () => boolean
+    maxDeadlineIncrease: number
+    maxDeadlineDecrease: number
   }
   handleStart: () => void
   handleStop: () => void
@@ -121,6 +123,8 @@ export const Workspace: FC<React.PropsWithChildren<WorkspaceProps>> = ({
               onDeadlinePlus={scheduleProps.onDeadlinePlus}
               deadlineMinusEnabled={scheduleProps.deadlineMinusEnabled}
               deadlinePlusEnabled={scheduleProps.deadlinePlusEnabled}
+              maxDeadlineDecrease={scheduleProps.maxDeadlineDecrease}
+              maxDeadlineIncrease={scheduleProps.maxDeadlineIncrease}
               canUpdateWorkspace={canUpdateWorkspace}
             />
             <WorkspaceActions
diff --git a/site/src/components/WorkspaceScheduleButton/EditHours.tsx b/site/src/components/WorkspaceScheduleButton/EditHours.tsx
new file mode 100644
index 0000000000000..5bcd34a710054
--- /dev/null
+++ b/site/src/components/WorkspaceScheduleButton/EditHours.tsx
@@ -0,0 +1,53 @@
+import Button from "@material-ui/core/Button"
+import { makeStyles } from "@material-ui/core/styles"
+import TextField from "@material-ui/core/TextField"
+import { Stack } from "components/Stack/Stack"
+import { useState } from "react"
+import { useTranslation } from "react-i18next"
+
+interface EditHoursProps {
+  handleSubmit: (hours: number) => void
+  max: number
+}
+
+export const EditHours = ({
+  handleSubmit,
+  max,
+}: EditHoursProps): JSX.Element => {
+  const { t } = useTranslation("workspacePage")
+  const [hours, setHours] = useState(1)
+  const styles = useStyles()
+
+  return (
+    <form onSubmit={() => handleSubmit(hours)}>
+      <Stack direction="row" alignItems="baseline" spacing={1}>
+        <TextField
+          className={styles.inputField}
+          inputProps={{ min: 0, max, step: 1 }}
+          label={t("workspaceScheduleButton.hours")}
+          value={hours}
+          onChange={(e) => setHours(parseInt(e.target.value))}
+          type="number"
+        />
+        <Button className={styles.button} type="submit" color="primary">
+          {t("workspaceScheduleButton.submitDeadline")}
+        </Button>
+      </Stack>
+    </form>
+  )
+}
+
+const useStyles = makeStyles(() => ({
+  inputField: {
+    width: "70px",
+    "& .MuiOutlinedInput-root": {
+      height: "30px",
+    },
+  },
+  button: {
+    "&.MuiButton-root": {
+      minHeight: "30px",
+      height: "30px",
+    },
+  },
+}))
diff --git a/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.stories.tsx b/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.stories.tsx
index 043c53da948bc..033c9698ced01 100644
--- a/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.stories.tsx
+++ b/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.stories.tsx
@@ -16,6 +16,12 @@ export default {
     canUpdateWorkspace: {
       defaultValue: true,
     },
+    deadlineMinusEnabled: {
+      defaultValue: (): boolean => false,
+    },
+    deadlinePlusEnabled: {
+      defaultValue: (): boolean => false,
+    },
   },
 }
 
@@ -64,6 +70,7 @@ WorkspaceOffShort.args = {
 
 export const WorkspaceOffLong = Template.bind({})
 WorkspaceOffLong.args = {
+  deadlinePlusEnabled: () => true,
   workspace: {
     ...Mocks.MockWorkspace,
 
diff --git a/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.test.tsx b/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.test.tsx
index 8e0d4e53583f1..5ee401f7be56b 100644
--- a/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.test.tsx
+++ b/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.test.tsx
@@ -2,7 +2,7 @@ import dayjs from "dayjs"
 import utc from "dayjs/plugin/utc"
 import * as TypesGen from "../../api/typesGenerated"
 import * as Mocks from "../../testHelpers/entities"
-import { shouldDisplayPlusMinus } from "./WorkspaceScheduleButton"
+import { canEditDeadline } from "./WorkspaceScheduleButton"
 
 dayjs.extend(utc)
 
@@ -13,7 +13,7 @@ describe("WorkspaceScheduleButton", () => {
       const workspace: TypesGen.Workspace = Mocks.MockStoppedWorkspace
 
       // Then: shouldDisplayPlusMinus should be false
-      expect(shouldDisplayPlusMinus(workspace)).toBeFalsy()
+      expect(canEditDeadline(workspace)).toBeFalsy()
     })
 
     it("should display if the workspace is running", () => {
@@ -21,7 +21,7 @@ describe("WorkspaceScheduleButton", () => {
       const workspace: TypesGen.Workspace = Mocks.MockWorkspace
 
       // Then: shouldDisplayPlusMinus should be false
-      expect(shouldDisplayPlusMinus(workspace)).toBeTruthy()
+      expect(canEditDeadline(workspace)).toBeTruthy()
     })
   })
 })
diff --git a/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.tsx b/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.tsx
index 66e3df5e3075e..b613786910ca6 100644
--- a/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.tsx
+++ b/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleButton.tsx
@@ -1,11 +1,13 @@
 import Button from "@material-ui/core/Button"
 import IconButton from "@material-ui/core/IconButton"
 import Popover from "@material-ui/core/Popover"
-import { makeStyles } from "@material-ui/core/styles"
+import { makeStyles, Theme } from "@material-ui/core/styles"
 import Tooltip from "@material-ui/core/Tooltip"
 import AddIcon from "@material-ui/icons/Add"
 import RemoveIcon from "@material-ui/icons/Remove"
 import ScheduleIcon from "@material-ui/icons/Schedule"
+import { Maybe } from "components/Conditionals/Maybe"
+import { Stack } from "components/Stack/Stack"
 import dayjs from "dayjs"
 import advancedFormat from "dayjs/plugin/advancedFormat"
 import duration from "dayjs/plugin/duration"
@@ -17,6 +19,7 @@ import { useTranslation } from "react-i18next"
 import { Workspace } from "../../api/typesGenerated"
 import { isWorkspaceOn } from "../../util/workspace"
 import { WorkspaceSchedule } from "../WorkspaceSchedule/WorkspaceSchedule"
+import { EditHours } from "./EditHours"
 import { WorkspaceScheduleLabel } from "./WorkspaceScheduleLabel"
 
 // REMARK: some plugins depend on utc, so it's listed first. Otherwise they're
@@ -27,12 +30,12 @@ dayjs.extend(duration)
 dayjs.extend(relativeTime)
 dayjs.extend(timezone)
 
-export const shouldDisplayPlusMinus = (workspace: Workspace): boolean => {
+export const canEditDeadline = (workspace: Workspace): boolean => {
   return isWorkspaceOn(workspace) && Boolean(workspace.latest_build.deadline)
 }
 
 export const shouldDisplayScheduleLabel = (workspace: Workspace): boolean => {
-  if (shouldDisplayPlusMinus(workspace)) {
+  if (canEditDeadline(workspace)) {
     return true
   }
   if (isWorkspaceOn(workspace)) {
@@ -43,13 +46,17 @@ export const shouldDisplayScheduleLabel = (workspace: Workspace): boolean => {
 
 export interface WorkspaceScheduleButtonProps {
   workspace: Workspace
-  onDeadlinePlus: () => void
-  onDeadlineMinus: () => void
+  onDeadlinePlus: (hours: number) => void
+  onDeadlineMinus: (hours: number) => void
   deadlineMinusEnabled: () => boolean
   deadlinePlusEnabled: () => boolean
+  maxDeadlineIncrease: number
+  maxDeadlineDecrease: number
   canUpdateWorkspace: boolean
 }
 
+export type EditMode = "add" | "subtract" | "off"
+
 export const WorkspaceScheduleButton: React.FC<
   WorkspaceScheduleButtonProps
 > = ({
@@ -58,49 +65,93 @@ export const WorkspaceScheduleButton: React.FC<
   onDeadlineMinus,
   deadlinePlusEnabled,
   deadlineMinusEnabled,
+  maxDeadlineDecrease,
+  maxDeadlineIncrease,
   canUpdateWorkspace,
 }) => {
   const { t } = useTranslation("workspacePage")
   const anchorRef = useRef<HTMLButtonElement>(null)
   const [isOpen, setIsOpen] = useState(false)
+  const [editMode, setEditMode] = useState<EditMode>("off")
   const id = isOpen ? "schedule-popover" : undefined
-  const styles = useStyles()
+  const styles = useStyles({ editMode })
 
   const onClose = () => {
     setIsOpen(false)
   }
 
+  const handleSubmitHours = (hours: number) => {
+    if (hours !== 0) {
+      if (editMode === "add") {
+        onDeadlinePlus(hours)
+      }
+      if (editMode === "subtract") {
+        onDeadlineMinus(hours)
+      }
+    }
+    setEditMode("off")
+  }
+
   return (
     <span className={styles.wrapper}>
-      {shouldDisplayScheduleLabel(workspace) && (
-        <span className={styles.label}>
-          <WorkspaceScheduleLabel workspace={workspace} />
-          {canUpdateWorkspace && shouldDisplayPlusMinus(workspace) && (
-            <span className={styles.actions}>
-              <IconButton
-                className={styles.iconButton}
-                size="small"
-                disabled={!deadlineMinusEnabled()}
-                onClick={onDeadlineMinus}
-              >
-                <Tooltip title={t("workspaceScheduleButton.editDeadlineMinus")}>
-                  <RemoveIcon />
-                </Tooltip>
-              </IconButton>
-              <IconButton
-                className={styles.iconButton}
-                size="small"
-                disabled={!deadlinePlusEnabled()}
-                onClick={onDeadlinePlus}
-              >
-                <Tooltip title={t("workspaceScheduleButton.editDeadlinePlus")}>
-                  <AddIcon />
-                </Tooltip>
-              </IconButton>
-            </span>
-          )}
-        </span>
-      )}
+      <Maybe condition={shouldDisplayScheduleLabel(workspace)}>
+        <Stack
+          className={styles.label}
+          spacing={1}
+          direction="row"
+          alignItems="center"
+        >
+          <Stack spacing={1} direction="row" alignItems="center">
+            <WorkspaceScheduleLabel workspace={workspace} />
+            <Maybe condition={canUpdateWorkspace && canEditDeadline(workspace)}>
+              <span className={styles.actions}>
+                <IconButton
+                  className={styles.subtractButton}
+                  size="small"
+                  disabled={!deadlineMinusEnabled()}
+                  onClick={() => {
+                    setEditMode("subtract")
+                  }}
+                >
+                  <Tooltip
+                    title={t("workspaceScheduleButton.editDeadlineMinus")}
+                  >
+                    <RemoveIcon />
+                  </Tooltip>
+                </IconButton>
+                <IconButton
+                  className={styles.addButton}
+                  size="small"
+                  disabled={!deadlinePlusEnabled()}
+                  onClick={() => {
+                    setEditMode("add")
+                  }}
+                >
+                  <Tooltip
+                    title={t("workspaceScheduleButton.editDeadlinePlus")}
+                  >
+                    <AddIcon />
+                  </Tooltip>
+                </IconButton>
+              </span>
+            </Maybe>
+          </Stack>
+          <Maybe
+            condition={
+              canUpdateWorkspace &&
+              canEditDeadline(workspace) &&
+              editMode !== "off"
+            }
+          >
+            <EditHours
+              handleSubmit={handleSubmitHours}
+              max={
+                editMode === "add" ? maxDeadlineIncrease : maxDeadlineDecrease
+              }
+            />
+          </Maybe>
+        </Stack>
+      </Maybe>
       <>
         <Button
           ref={anchorRef}
@@ -139,7 +190,11 @@ export const WorkspaceScheduleButton: React.FC<
   )
 }
 
-const useStyles = makeStyles((theme) => ({
+interface StyleProps {
+  editMode: EditMode
+}
+
+const useStyles = makeStyles<Theme, StyleProps>((theme) => ({
   wrapper: {
     display: "inline-flex",
     alignItems: "center",
@@ -151,15 +206,13 @@ const useStyles = makeStyles((theme) => ({
     },
   },
   label: {
-    borderRight: 0,
-    padding: "0 8px 0 16px",
+    padding: theme.spacing(0, 2),
     color: theme.palette.text.secondary,
 
     [theme.breakpoints.down("sm")]: {
       width: "100%",
-      display: "flex",
-      alignItems: "center",
       padding: theme.spacing(1.5, 2),
+      flexDirection: "column",
     },
   },
   actions: {
@@ -190,8 +243,19 @@ const useStyles = makeStyles((theme) => ({
       },
     },
   },
-  iconButton: {
+  addButton: {
+    borderRadius: theme.shape.borderRadius,
+    border: ({ editMode }) =>
+      editMode === "add"
+        ? `2px solid ${theme.palette.primary.main}`
+        : "2px solid transparent",
+  },
+  subtractButton: {
     borderRadius: theme.shape.borderRadius,
+    border: ({ editMode }) =>
+      editMode === "subtract"
+        ? `2px solid ${theme.palette.primary.main}`
+        : "2px solid transparent",
   },
   popoverPaper: {
     padding: `${theme.spacing(2)}px ${theme.spacing(3)}px ${theme.spacing(
diff --git a/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleLabel.tsx b/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleLabel.tsx
index a2b3146d95788..78c9df4ecbf3f 100644
--- a/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleLabel.tsx
+++ b/site/src/components/WorkspaceScheduleButton/WorkspaceScheduleLabel.tsx
@@ -1,11 +1,13 @@
 import { makeStyles } from "@material-ui/core/styles"
+import { ChooseOne, Cond } from "components/Conditionals/ChooseOne"
+import { Maybe } from "components/Conditionals/Maybe"
+import { useTranslation } from "react-i18next"
 import { Workspace } from "../../api/typesGenerated"
 import { combineClasses } from "../../util/combineClasses"
 import {
   autoStartDisplay,
   autoStopDisplay,
   isShuttingDown,
-  Language,
 } from "../../util/schedule"
 import { isWorkspaceOn } from "../../util/workspace"
 
@@ -13,33 +15,38 @@ export const WorkspaceScheduleLabel: React.FC<{ workspace: Workspace }> = ({
   workspace,
 }) => {
   const styles = useStyles()
-
-  if (isWorkspaceOn(workspace)) {
-    const stopLabel = autoStopDisplay(workspace)
-    const shouldDisplayStrongLabel = !isShuttingDown(workspace)
-
-    // If it is shutting down, we don't need to display the auto stop label
-    return (
-      <span className={combineClasses([styles.labelText, "chromatic-ignore"])}>
-        {shouldDisplayStrongLabel && <strong>{Language.autoStopLabel}</strong>}{" "}
-        <span className={styles.value}>{stopLabel}</span>
-      </span>
-    )
-  }
+  const { t } = useTranslation("common")
 
   return (
-    <span className={combineClasses([styles.labelText, "chromatic-ignore"])}>
-      <strong>{Language.autoStartLabel}</strong>{" "}
-      <span className={styles.value}>
-        {autoStartDisplay(workspace.autostart_schedule)}
-      </span>
-    </span>
+    <ChooseOne>
+      <Cond condition={isWorkspaceOn(workspace)}>
+        <span
+          className={combineClasses([styles.labelText, "chromatic-ignore"])}
+        >
+          <Maybe condition={!isShuttingDown(workspace)}>
+            <strong>{t("schedule.autoStopLabel")}</strong>
+          </Maybe>{" "}
+          <span className={styles.value}>{autoStopDisplay(workspace)}</span>
+        </span>
+      </Cond>
+      <Cond>
+        <span
+          className={combineClasses([styles.labelText, "chromatic-ignore"])}
+        >
+          <strong>{t("schedule.autoStartLabel")}</strong>{" "}
+          <span className={styles.value}>
+            {autoStartDisplay(workspace.autostart_schedule)}
+          </span>
+        </span>
+      </Cond>
+    </ChooseOne>
   )
 }
 
 const useStyles = makeStyles((theme) => ({
   labelText: {
-    marginRight: theme.spacing(2),
+    marginRight: theme.spacing(1),
+    marginLeft: theme.spacing(1),
     lineHeight: "160%",
 
     [theme.breakpoints.down("sm")]: {
diff --git a/site/src/i18n/en/common.json b/site/src/i18n/en/common.json
index 95db9bfc3e547..463a8176bf164 100644
--- a/site/src/i18n/en/common.json
+++ b/site/src/i18n/en/common.json
@@ -19,6 +19,10 @@
     "confirmLabel": "Name of {{entity}} to delete",
     "incorrectName": "Incorrect {{entity}} name."
   },
+  "schedule": {
+    "autoStartLabel": "Starts at",
+    "autoStopLabel": "Stops at"
+  },
   "ctas": {
     "dismissCta": "Dismiss",
     "expand": "Click here to learn more",
diff --git a/site/src/i18n/en/workspacePage.json b/site/src/i18n/en/workspacePage.json
index 781e03121ef42..8f36e9b3d44e6 100644
--- a/site/src/i18n/en/workspacePage.json
+++ b/site/src/i18n/en/workspacePage.json
@@ -4,8 +4,10 @@
   },
   "workspaceScheduleButton": {
     "schedule": "Schedule",
-    "editDeadlineMinus": "Subtract one hour",
-    "editDeadlinePlus": "Add one hour"
+    "editDeadlineMinus": "Subtract hours",
+    "editDeadlinePlus": "Add hours",
+    "submitDeadline": "Set",
+    "hours": "Hours"
   },
   "ctas": {
     "createWorkspaceCta": "Create new workspace",
diff --git a/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx b/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
index 300ec5ca92e74..b695523a31327 100644
--- a/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
@@ -4,6 +4,11 @@ import dayjs from "dayjs"
 import { useContext } from "react"
 import { Helmet } from "react-helmet-async"
 import { useTranslation } from "react-i18next"
+import {
+  getMaxDeadline,
+  getMaxDeadlineChange,
+  getMinDeadline,
+} from "util/schedule"
 import { selectFeatureVisibility } from "xServices/entitlements/entitlementsSelectors"
 import { StateFrom } from "xstate"
 import { DeleteDialog } from "../../components/Dialogs/DeleteDialog/DeleteDialog"
@@ -31,6 +36,7 @@ export const WorkspaceReadyPage = ({
   const [bannerState, bannerSend] = useActor(
     workspaceState.children["scheduleBannerMachine"],
   )
+  const deadline = bannerState.context.deadline
   const xServices = useContext(XServiceContext)
   const featureVisibility = useSelector(
     xServices.entitlementsXService,
@@ -39,6 +45,7 @@ export const WorkspaceReadyPage = ({
   const [buildInfoState] = useActor(xServices.buildInfoXService)
   const {
     workspace,
+    template,
     refreshWorkspaceWarning,
     builds,
     getBuildsError,
@@ -81,20 +88,30 @@ export const WorkspaceReadyPage = ({
           },
         }}
         scheduleProps={{
-          onDeadlineMinus: () => {
+          onDeadlineMinus: (hours: number) => {
             bannerSend({
               type: "DECREASE_DEADLINE",
-              hours: 1,
+              hours,
             })
           },
-          onDeadlinePlus: () => {
+          onDeadlinePlus: (hours: number) => {
             bannerSend({
               type: "INCREASE_DEADLINE",
-              hours: 1,
+              hours,
             })
           },
           deadlineMinusEnabled: () => !bannerState.matches("atMinDeadline"),
           deadlinePlusEnabled: () => !bannerState.matches("atMaxDeadline"),
+          maxDeadlineDecrease: deadline
+            ? getMaxDeadlineChange(deadline, getMinDeadline())
+            : 0,
+          maxDeadlineIncrease:
+            deadline && template
+              ? getMaxDeadlineChange(
+                  getMaxDeadline(workspace, template),
+                  deadline,
+                )
+              : 0,
         }}
         isUpdating={workspaceState.hasTag("updating")}
         workspace={workspace}
diff --git a/site/src/util/schedule.test.ts b/site/src/util/schedule.test.ts
index dc25996cc4517..9cd3dd1b50177 100644
--- a/site/src/util/schedule.test.ts
+++ b/site/src/util/schedule.test.ts
@@ -9,6 +9,7 @@ import {
   deadlineExtensionMin,
   extractTimezone,
   getMaxDeadline,
+  getMaxDeadlineChange,
   getMinDeadline,
   stripTimezone,
 } from "./schedule"
@@ -124,3 +125,19 @@ describe("canReduceDeadline", () => {
     expect(canReduceDeadline(dayjs().add(100, "years"))).toBeTruthy()
   })
 })
+
+describe("getMaxDeadlineChange", () => {
+  it("should return the number of hours you can add before hitting the max deadline", () => {
+    const deadline = dayjs()
+    const maxDeadline = dayjs().add(1, "hour").add(40, "minutes")
+    // you can only add one hour even though the max is 1:40 away
+    expect(getMaxDeadlineChange(deadline, maxDeadline)).toEqual(1)
+  })
+
+  it("should return the number of hours you can subtract before hitting the min deadline", () => {
+    const deadline = dayjs().add(2, "hours").add(40, "minutes")
+    const minDeadline = dayjs()
+    // you can only subtract 2 hours even though the min is 2:40 less
+    expect(getMaxDeadlineChange(deadline, minDeadline)).toEqual(2)
+  })
+})
diff --git a/site/src/util/schedule.ts b/site/src/util/schedule.ts
index 75e3f849718a8..c96ba02daa47f 100644
--- a/site/src/util/schedule.ts
+++ b/site/src/util/schedule.ts
@@ -167,3 +167,15 @@ export function canReduceDeadline(deadline: dayjs.Dayjs): boolean {
 
 export const getDeadline = (workspace: Workspace): dayjs.Dayjs =>
   dayjs(workspace.latest_build.deadline).utc()
+
+/**
+ * Get number of hours you can add or subtract to the current deadline before hitting the max or min deadline.
+ * @param deadline
+ * @param workspace
+ * @param template
+ * @returns number, in hours
+ */
+export const getMaxDeadlineChange = (
+  deadline: dayjs.Dayjs,
+  extremeDeadline: dayjs.Dayjs,
+): number => Math.abs(deadline.diff(extremeDeadline, "hours"))