diff --git a/.github/workflows/deploy-prod.yml b/.github/workflows/deploy-prod.yml
index c70265c7753f..b71406902069 100644
--- a/.github/workflows/deploy-prod.yml
+++ b/.github/workflows/deploy-prod.yml
@@ -18,18 +18,30 @@ jobs:
 
       - uses: microsoft/playwright-github-action@v1
 
-      # Build v2
-      - name: Build website v2
+      # Builds the modules, and boostraps the other modules
+      - name: Build website
         run: |
           yarn install
           yarn docs-sync pull microsoft/TypeScript-Website-localizations#main 1
           yarn bootstrap
           yarn build
-          yarn build-site
-          cp -r packages/typescriptlang-org/public site
         env:
           YARN_CHECKSUM_BEHAVIOR: ignore
 
+      # Update the site plan, scoped out on its own because it gets access to secrets
+      - run: node packages/typescriptlang-org/scripts/getTypeScriptReleasePlan.js
+        env:
+          GITHUB_BOT_TOKEN: ${{ secrets.GITHUB_BOT_TOKEN }}
+          TEAMS_WEB_BOT_INCOMING_URL: ${{ secrets.TEAMS_WEB_BOT_INCOMING_URL }}
+
+      # Builds the site
+      -  name: Makes the site
+         run: |
+           yarn build-site
+           cp -r packages/typescriptlang-org/public site
+         env:
+          YARN_CHECKSUM_BEHAVIOR: ignore
+
       # Deploy to the prod appservice
       - name: Deploy + Publish to AppService
         uses: peaceiris/actions-gh-pages@v1.1.0
diff --git a/packages/typescriptlang-org/scripts/getTypeScriptNPMVersions.js b/packages/typescriptlang-org/scripts/getTypeScriptNPMVersions.js
index 366ee89a0c72..a97fe354d50f 100644
--- a/packages/typescriptlang-org/scripts/getTypeScriptNPMVersions.js
+++ b/packages/typescriptlang-org/scripts/getTypeScriptNPMVersions.js
@@ -126,6 +126,11 @@ const getTypeScriptNPMVersions = async () => {
     ? siteReleaseNotesURL
     : releasePostURL
 
+  const next =
+    semver.minor(stable) == 9
+      ? `${semver.major(stable) + 1}.${semver.minor(stable)}`
+      : `${semver.major(stable)}.${semver.minor(stable) + 1}`
+
   return {
     tags: {
       stableMajMin: `${semver.major(stable)}.${semver.minor(stable)}`,
@@ -134,6 +139,7 @@ const getTypeScriptNPMVersions = async () => {
       beta,
       rc,
       rcMajMin: `${semver.major(rc)}.${semver.minor(rc)}`,
+      next,
     },
     isRC,
     isBeta,
diff --git a/packages/typescriptlang-org/scripts/getTypeScriptReleasePlan.js b/packages/typescriptlang-org/scripts/getTypeScriptReleasePlan.js
new file mode 100644
index 000000000000..f95a163c6520
--- /dev/null
+++ b/packages/typescriptlang-org/scripts/getTypeScriptReleasePlan.js
@@ -0,0 +1,121 @@
+// This script relies on getTypeScriptNPMVersions.js having been ran already
+// it will grab the latest TypeScript issue with info about the iteration plan
+// and turn that into structured data.
+
+// node packages/typescriptlang-org/scripts/getTypeScriptReleasePlan.js
+
+const Octokit = require("@octokit/rest")
+const versionMeta = require("../src/lib/release-info.json")
+const fetch = require("node-fetch")
+const { format } = require("prettier")
+const { writeFileSync } = require("fs")
+const { join } = require("path")
+
+const token = process.env.GITHUB_BOT_TOKEN || process.env.GITHUB_TOKEN
+if (!token) throw new Error("No GitHub Token at process.env.GITHUB_BOT_TOKEN")
+
+const go = async () => {
+  const octokit = new Octokit({
+    auth: token,
+    userAgent: "TS Website Issue Searcher",
+  })
+
+  const issues = await octokit.search.issuesAndPullRequests({
+    q: "iteration plan repo:microsoft/typescript state:open type:issues",
+  })
+
+  const upcoming = issues.data.items.find(
+    i =>
+      i.title.toLowerCase().includes(versionMeta.tags.next) &&
+      i.labels.find(l => l.name === "Planning")
+  )
+
+  // Couldn't find the issue, bail,
+  if (!upcoming) {
+    return sendTeamsFail(
+      `Could not find an iteration plan issue for ${versionMeta.tags.next} during the most recent site deploy - see https://github.com/microsoft/TypeScript-website/blob/v2/packages/typescriptlang-org/scripts/getTypeScriptReleaseInfo.js`
+    )
+  }
+
+  const lines = upcoming.body.toLowerCase().split("\n")
+  const lastRelease = lines.find(
+    l =>
+      l.includes(`${versionMeta.tags.stableMajMin} release`) && l.includes("|")
+  )
+  const beta = lines.find(
+    l => l.includes(`${versionMeta.tags.next} beta release`) && l.includes("|")
+  )
+
+  const rc = lines.find(
+    l => l.includes(`${versionMeta.tags.next} rc release`) && l.includes("|")
+  )
+
+  const release = lines.find(
+    l => l.includes(`${versionMeta.tags.next} final release`) && l.includes("|")
+  )
+
+  // Making sure we got good data
+  const dates = {
+    lastRelease,
+    beta,
+    rc,
+    release,
+  }
+  const missing = []
+  Object.keys(dates).forEach(key => {
+    if (!dates[key]) {
+      missing.push(key)
+    }
+  })
+  if (missing.length) {
+    // prettier-ignore
+    return sendTeamsFail(`Could not parse the md table for ${missing.join(",")} in https://github.com/microsoft/TypeScript/issues/${upcoming.number} - see https://github.com/microsoft/TypeScript-website/blob/v2/packages/typescriptlang-org/scripts/getTypeScriptReleaseInfo.js`)
+  }
+
+  // "june 29th      | **typescript 4.4 beta release**\r" -> Date
+  const toDate = str => {
+    const date = str.split("|")[0].trim()
+    const components = date.split(" ")
+    const month = components[0]
+    const day = components[1].replace("th", "").replace("st", "")
+    const thisYear = new Date().getFullYear()
+    const year = parseInt(components[2]) || thisYear
+    return new Date(`${month} ${day} ${year}`).toISOString()
+  }
+
+  const results = {
+    "_generated by":
+      "node packages/typescriptlang-org/scripts/getTypeScriptReleasePlan.js",
+    upcoming_version: versionMeta.tags.next,
+    iteration_plan_url: `https://github.com/microsoft/TypeScript/issues/${upcoming.number}`,
+    last_release_date: toDate(lastRelease),
+    upcoming_beta_date: toDate(beta),
+    upcoming_rc_date: toDate(rc),
+    upcoming_release_date: toDate(release),
+  }
+  const jsonPath = join(__dirname, "..", "src", "lib", "release-plan.json")
+
+  writeFileSync(
+    jsonPath,
+    format(JSON.stringify(results), { filepath: jsonPath })
+  )
+}
+
+go()
+
+const sendTeamsFail = title => {
+  const teamsURL = process.env.TEAMS_WEB_BOT_INCOMING_URL
+  const message = {
+    "@type": "MessageCard",
+    "@context": "https://schema.org/extensions",
+    summary: "Website issue",
+    themeColor: "0078D7",
+    title,
+  }
+
+  fetch(teamsURL, {
+    method: "post",
+    body: JSON.stringify(message),
+    headers: { "Content-Type": "application/json" },
+  })
+}
diff --git a/packages/typescriptlang-org/src/lib/release-plan.json b/packages/typescriptlang-org/src/lib/release-plan.json
index b4c408bb8494..fff3abb95116 100644
--- a/packages/typescriptlang-org/src/lib/release-plan.json
+++ b/packages/typescriptlang-org/src/lib/release-plan.json
@@ -1,9 +1,9 @@
 {
-  "_format": "mm/dd/yyyy - these get put into new Date()",
+  "_generated by": "node packages/typescriptlang-org/scripts/getTypeScriptReleaseInfo.js",
   "upcoming_version": "4.4",
   "iteration_plan_url": "https://github.com/microsoft/TypeScript/issues/44237",
-  "last_release_date": "05/25/2021",
-  "upcoming_beta_date": "06/25/2021",
-  "upcoming_rc_date": "07/06/2021",
-  "upcoming_release_date": "07/24/2021"
+  "last_release_date": "2021-05-24T23:00:00.000Z",
+  "upcoming_beta_date": "2021-06-28T23:00:00.000Z",
+  "upcoming_rc_date": "2021-08-09T23:00:00.000Z",
+  "upcoming_release_date": "2021-08-23T23:00:00.000Z"
 }