diff --git a/site/src/components/WorkspaceSchedule/WorkspaceSchedule.tsx b/site/src/components/WorkspaceSchedule/WorkspaceSchedule.tsx
index 1a5d35a499f11..5d5d1db960c5c 100644
--- a/site/src/components/WorkspaceSchedule/WorkspaceSchedule.tsx
+++ b/site/src/components/WorkspaceSchedule/WorkspaceSchedule.tsx
@@ -17,8 +17,10 @@ import { stripTimezone } from "../../util/schedule"
 import { isWorkspaceOn } from "../../util/workspace"
 import { Stack } from "../Stack/Stack"
 
-dayjs.extend(advancedFormat)
+// REMARK: some plugins depend on utc, so it's listed first. Otherwise they're
+//         sorted alphabetically.
 dayjs.extend(utc)
+dayjs.extend(advancedFormat)
 dayjs.extend(duration)
 dayjs.extend(relativeTime)
 dayjs.extend(timezone)
@@ -50,7 +52,7 @@ export const Language = {
       if (now.isAfter(deadline)) {
         return "Workspace is shutting down"
       } else {
-        return deadline.tz(dayjs.tz.guess()).format("hh:mm A")
+        return deadline.tz(dayjs.tz.guess()).format("MMM D, YYYY h:mm A")
       }
     } else if (!ttl || ttl < 1) {
       // If the workspace is not on, and the ttl is 0 or undefined, then the
diff --git a/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.stories.tsx b/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.stories.tsx
index c9ea6eafa8b9d..5c3126fc74248 100644
--- a/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.stories.tsx
+++ b/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.stories.tsx
@@ -22,7 +22,7 @@ export const WorkspaceNotRunning = Template.bind({})
 WorkspaceNotRunning.args = {
   now: dayjs("2022-05-17T17:40:00Z"),
   initialValues: {
-    ...defaultWorkspaceSchedule(5, "asdfasdf"),
+    ...defaultWorkspaceSchedule(5),
     timezone: "UTC",
   },
   workspace: {
@@ -41,7 +41,7 @@ export const WorkspaceWillNotShutDown = Template.bind({})
 WorkspaceWillNotShutDown.args = {
   now: dayjs("2022-05-17T17:40:00Z"),
   initialValues: {
-    ...defaultWorkspaceSchedule(5, "asdfasdf"),
+    ...defaultWorkspaceSchedule(5),
     timezone: "UTC",
     ttl: 0,
   },
@@ -60,7 +60,7 @@ export const WorkspaceWillShutdown = Template.bind({})
 WorkspaceWillShutdown.args = {
   now: dayjs("2022-05-17T17:40:00Z"),
   initialValues: {
-    ...defaultWorkspaceSchedule(5, "asdfasdf"),
+    ...defaultWorkspaceSchedule(5),
     timezone: "UTC",
   },
   workspace: {
@@ -76,9 +76,9 @@ WorkspaceWillShutdown.args = {
 
 export const WorkspaceWillShutdownSoon = Template.bind({})
 WorkspaceWillShutdownSoon.args = {
-  now: dayjs("2022-05-17T18:10:00Z"),
+  now: dayjs("2022-05-17T16:39:00Z"),
   initialValues: {
-    ...defaultWorkspaceSchedule(5, "asdfasdf"),
+    ...defaultWorkspaceSchedule(2),
     timezone: "UTC",
     ttl: 1,
   },
@@ -86,8 +86,9 @@ WorkspaceWillShutdownSoon.args = {
     ...Mocks.MockWorkspace,
     latest_build: {
       ...Mocks.MockWorkspaceBuild,
-      updated_at: "2022-05-17T17:39:00Z",
+      deadline: "2022-05-17T18:09:00Z",
     },
+    ttl_ms: 2 * 60 * 60 * 1000, // 2 hours = shuts off at 18:09
   },
   onCancel: () => action("onCancel"),
   onSubmit: () => action("onSubmit"),
@@ -95,9 +96,9 @@ WorkspaceWillShutdownSoon.args = {
 
 export const WorkspaceWillShutdownImmediately = Template.bind({})
 WorkspaceWillShutdownImmediately.args = {
-  now: dayjs("2022-05-17T18:40:00Z"),
+  now: dayjs("2022-05-17T17:09:00Z"),
   initialValues: {
-    ...defaultWorkspaceSchedule(5, "asdfasdf"),
+    ...defaultWorkspaceSchedule(1),
     timezone: "UTC",
     ttl: 1,
   },
@@ -105,8 +106,9 @@ WorkspaceWillShutdownImmediately.args = {
     ...Mocks.MockWorkspace,
     latest_build: {
       ...Mocks.MockWorkspaceBuild,
-      updated_at: "2022-05-17T17:39:00Z",
+      deadline: "2022-05-17T18:09:00Z",
     },
+    ttl_ms: 2 * 60 * 60 * 1000, // 2 hours = shuts off at 18:09
   },
   onCancel: () => action("onCancel"),
   onSubmit: () => action("onSubmit"),
diff --git a/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.test.ts b/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.test.ts
index 8fa25cc66abd3..3e37484b9c09b 100644
--- a/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.test.ts
+++ b/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.test.ts
@@ -160,31 +160,99 @@ describe("validationSchema", () => {
 })
 
 describe("ttlShutdownAt", () => {
-  it.each<[dayjs.Dayjs, Workspace, string, number, string]>([
-    [dayjs("2022-05-17T18:09:00Z"), Mocks.MockStoppedWorkspace, "America/Chicago", 1, Language.ttlHelperText],
-    [dayjs("2022-05-17T18:09:00Z"), Mocks.MockWorkspace, "America/Chicago", 0, Language.ttlCausesNoShutdownHelperText],
+  it.each<[string, dayjs.Dayjs, Workspace, string, number, string]>([
     [
+      "Workspace is stopped --> helper text",
       dayjs("2022-05-17T18:09:00Z"),
-      Mocks.MockWorkspace,
+      Mocks.MockStoppedWorkspace,
       "America/Chicago",
       1,
-      `${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownAt} 01:39 PM CDT.`,
+      Language.ttlHelperText,
     ],
     [
-      dayjs("2022-05-17T18:10:00Z"),
+      "TTL is not modified --> helper text",
+      dayjs("2022-05-17T16:09:00Z"),
+      {
+        ...Mocks.MockWorkspace,
+        latest_build: {
+          ...Mocks.MockWorkspaceBuild,
+          deadline: "2022-05-17T18:09:00Z",
+        },
+        ttl_ms: 2 * 60 * 60 * 1000, // 2 hours = shuts off at 18:09
+      },
+      "America/Chicago",
+      2,
+      Language.ttlHelperText,
+    ],
+    [
+      "TTL becomes 0 --> manual helper text",
+      dayjs("2022-05-17T18:09:00Z"),
       Mocks.MockWorkspace,
       "America/Chicago",
+      0,
+      Language.ttlCausesNoShutdownHelperText,
+    ],
+    [
+      "Deadline of 18:09 becomes 17:09 at 17:09 --> immediate shutdown",
+      dayjs("2022-05-17T17:09:00Z"),
+      {
+        ...Mocks.MockWorkspace,
+        latest_build: {
+          ...Mocks.MockWorkspaceBuild,
+          deadline: "2022-05-17T18:09:00Z",
+        },
+        ttl_ms: 2 * 60 * 60 * 1000, // 2 hours = shuts off at 18:09
+      },
+      "America/Chicago",
+      1,
+      `⚠️ ${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownImmediately} ⚠️`,
+    ],
+    [
+      "Deadline of 18:09 becomes 17:09 at 16:39 --> display shutdown soon",
+      dayjs("2022-05-17T16:39:00Z"),
+      {
+        ...Mocks.MockWorkspace,
+        latest_build: {
+          ...Mocks.MockWorkspaceBuild,
+          deadline: "2022-05-17T18:09:00Z",
+        },
+        ttl_ms: 2 * 60 * 60 * 1000, // 2 hours = shuts off at 18:09
+      },
+      "America/Chicago",
       1,
       `⚠️ ${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownSoon} ⚠️`,
     ],
     [
-      dayjs("2022-05-17T18:40:00Z"),
-      Mocks.MockWorkspace,
+      "Deadline of 18:09 becomes 17:09 at 16:09 --> display 12:09 CDT",
+      dayjs("2022-05-17T16:09:00Z"),
+      {
+        ...Mocks.MockWorkspace,
+        latest_build: {
+          ...Mocks.MockWorkspaceBuild,
+          deadline: "2022-05-17T18:09:00Z",
+        },
+        ttl_ms: 2 * 60 * 60 * 1000, // 2 hours = shuts off at 18:09
+      },
       "America/Chicago",
       1,
-      `⚠️ ${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownImmediately} ⚠️`,
+      `${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownAt} May 17, 2022 12:09 PM.`,
+    ],
+    [
+      "Manual workspace gets new deadline of 18:09 at 17:09 --> display 1:09 CDT",
+      dayjs("2022-05-17T17:09:00Z"),
+      {
+        ...Mocks.MockWorkspace,
+        latest_build: {
+          ...Mocks.MockWorkspaceBuild,
+          deadline: "0001-01-01T00:00:00Z",
+        },
+        ttl_ms: 0,
+      },
+      "America/Chicago",
+      1,
+      `${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownAt} May 17, 2022 1:09 PM.`,
     ],
-  ])("ttlShutdownAt(%p, %p, %p, %p) returns %p", (now, workspace, timezone, ttlHours, expected) => {
+  ])("%p", (_, now, workspace, timezone, ttlHours, expected) => {
     expect(ttlShutdownAt(now, workspace, timezone, ttlHours)).toEqual(expected)
   })
 })
diff --git a/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.tsx b/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.tsx
index e5d5376596c94..efd2c78199e34 100644
--- a/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.tsx
+++ b/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.tsx
@@ -9,6 +9,7 @@ import makeStyles from "@material-ui/core/styles/makeStyles"
 import TextField from "@material-ui/core/TextField"
 import dayjs from "dayjs"
 import advancedFormat from "dayjs/plugin/advancedFormat"
+import isSameOrBefore from "dayjs/plugin/isSameOrBefore"
 import timezone from "dayjs/plugin/timezone"
 import utc from "dayjs/plugin/utc"
 import { useFormik } from "formik"
@@ -23,11 +24,11 @@ import { FullPageForm } from "../FullPageForm/FullPageForm"
 import { Stack } from "../Stack/Stack"
 import { zones } from "./zones"
 
-// REMARK: timezone plugin depends on UTC
-//
-// SEE: https://day.js.org/docs/en/timezone/timezone
-dayjs.extend(advancedFormat)
+// REMARK: some plugins depend on utc, so it's listed first. Otherwise they're
+//         sorted alphabetically.
 dayjs.extend(utc)
+dayjs.extend(advancedFormat)
+dayjs.extend(isSameOrBefore)
 dayjs.extend(timezone)
 
 export const Language = {
@@ -282,19 +283,29 @@ export const WorkspaceScheduleForm: FC<WorkspaceScheduleFormProps> = ({
   )
 }
 
-export const ttlShutdownAt = (now: dayjs.Dayjs, workspace: Workspace, tz: string, newTTL: number): string => {
-  const newDeadline = dayjs(workspace.latest_build.updated_at).add(newTTL, "hour")
-  if (!isWorkspaceOn(workspace)) {
+export const ttlShutdownAt = (now: dayjs.Dayjs, workspace: Workspace, tz: string, formTTL: number): string => {
+  // a manual shutdown has a deadline of '"0001-01-01T00:00:00Z"'
+  // SEE: #1834
+  const deadline = dayjs(workspace.latest_build.deadline).utc()
+  const hasDeadline = deadline.year() > 1
+  const ttl = workspace.ttl_ms ? workspace.ttl_ms / (1000 * 60 * 60) : 0
+  const delta = formTTL - ttl
+
+  if (delta === 0 || !isWorkspaceOn(workspace)) {
     return Language.ttlHelperText
-  } else if (newTTL === 0) {
+  } else if (formTTL === 0) {
     return Language.ttlCausesNoShutdownHelperText
-  } else if (newDeadline.isBefore(now)) {
-    return `⚠️ ${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownImmediately} ⚠️`
-  } else if (newDeadline.isBefore(now.add(30, "minute"))) {
-    return `⚠️ ${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownSoon} ⚠️`
   } else {
-    const newDeadlineString = newDeadline.tz(tz).format("hh:mm A z")
-    return `${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownAt} ${newDeadlineString}.`
+    const newDeadline = dayjs(hasDeadline ? deadline : now).add(delta, "hours")
+    if (newDeadline.isSameOrBefore(now)) {
+      return `⚠️ ${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownImmediately} ⚠️`
+    } else if (newDeadline.isSameOrBefore(now.add(30, "minutes"))) {
+      return `⚠️ ${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownSoon} ⚠️`
+    } else {
+      return `${Language.ttlCausesShutdownHelperText} ${Language.ttlCausesShutdownAt} ${newDeadline
+        .tz(tz)
+        .format("MMM D, YYYY h:mm A")}.`
+    }
   }
 }