diff --git a/Dockerfile b/Dockerfile
index 505f3dd3a4..5e9ae0c3b3 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -5,7 +5,7 @@
 # --------------------------------------------------------------------------------
 # To update the sha, run `docker pull node:$VERSION-alpine`
 # look for something like: `Digest: sha256:0123456789abcdef`
-FROM node:20-alpine@sha256:66c7d989b6dabba6b4305b88f40912679aebd9f387a5b16ffa76dfb9ae90b060 as base
+FROM node:20-alpine@sha256:66f7f89199daea88a6b5d5aadaa6d20f7a16a90fc35274deda8e901e267d4bd7 as base
 
 # This directory is owned by the node user
 ARG APP_HOME=/home/node/app
diff --git a/src/frame/middleware/context/context.ts b/src/frame/middleware/context/context.ts
index dbf3c8a6cd..439b3f3c54 100644
--- a/src/frame/middleware/context/context.ts
+++ b/src/frame/middleware/context/context.ts
@@ -35,6 +35,8 @@ export default async function contextualize(
 
   const context: Context = {}
   req.context = context
+  console.log('CREATING CONTEXT')
+
   req.context.process = { env: {} }
 
   // define each context property explicitly for code-search friendliness
diff --git a/src/frame/middleware/fast-head.js b/src/frame/middleware/fast-head.ts
similarity index 55%
rename from src/frame/middleware/fast-head.js
rename to src/frame/middleware/fast-head.ts
index 9887773331..3685f92b0b 100644
--- a/src/frame/middleware/fast-head.js
+++ b/src/frame/middleware/fast-head.ts
@@ -1,6 +1,10 @@
+import type { Response, NextFunction } from 'express'
+
+import type { ExtendedRequest } from '@/types'
 import { defaultCacheControl } from './cache-control.js'
 
-export default function fastHead(req, res, next) {
+export default function fastHead(req: ExtendedRequest, res: Response, next: NextFunction) {
+  if (!req.context) throw new Error('request is not contextualized')
   const { context } = req
   const { page } = context
   if (page) {
diff --git a/src/frame/middleware/favicons.js b/src/frame/middleware/favicons.ts
similarity index 86%
rename from src/frame/middleware/favicons.js
rename to src/frame/middleware/favicons.ts
index 1155f089c7..c3fafea883 100644
--- a/src/frame/middleware/favicons.js
+++ b/src/frame/middleware/favicons.ts
@@ -5,10 +5,19 @@
 // solution to serve this directly.
 import fs from 'fs'
 
+import type { Response, NextFunction } from 'express'
+
+import type { ExtendedRequest } from '@/types'
 import { SURROGATE_ENUMS, setFastlySurrogateKey } from './set-fastly-surrogate-key.js'
 import { assetCacheControl } from './cache-control.js'
 
-const MAP = {
+type IconConfig = {
+  contentType: string
+  buffer: () => Buffer
+}
+const MAP: {
+  [uri: string]: IconConfig
+} = {
   '/favicon.ico': {
     contentType: 'image/x-icon',
     buffer: getBuffer('assets/images/site/favicon.ico'),
@@ -35,8 +44,8 @@ MAP['/apple-touch-icon-precomposed.png'] = MAP['/apple-touch-icon.png']
 MAP['/apple-touch-icon-120x120-precomposed.png'] = MAP['/apple-touch-icon-120x120.png']
 MAP['/apple-touch-icon-152x152-precomposed.png'] = MAP['/apple-touch-icon-152x152.png']
 
-function getBuffer(filePath) {
-  let buffer
+function getBuffer(filePath: string) {
+  let buffer: Buffer
   if (!fs.existsSync(filePath)) {
     throw new Error(`${filePath} not found on disk`)
   }
@@ -51,7 +60,7 @@ function getBuffer(filePath) {
   }
 }
 
-export default function favicons(req, res, next) {
+export default function favicons(req: ExtendedRequest, res: Response, next: NextFunction) {
   if (!MAP[req.path]) return next()
 
   // This makes sure the CDN caching survives each production deployment.
diff --git a/src/frame/middleware/index.ts b/src/frame/middleware/index.ts
index e4c8f431e0..3b010aaf92 100644
--- a/src/frame/middleware/index.ts
+++ b/src/frame/middleware/index.ts
@@ -49,14 +49,14 @@ import features from '@/versions/middleware/features.js'
 import productExamples from './context/product-examples'
 import productGroups from './context/product-groups'
 import featuredLinks from '@/landings/middleware/featured-links'
-import learningTrack from '@/learning-track/middleware/learning-track.js'
+import learningTrack from '@/learning-track/middleware/learning-track'
 import next from './next.js'
 import renderPage from './render-page.js'
 import assetPreprocessing from '@/assets/middleware/asset-preprocessing'
 import archivedAssetRedirects from '@/archives/middleware/archived-asset-redirects'
-import favicons from './favicons.js'
+import favicons from './favicons'
 import setStaticAssetCaching from '@/assets/middleware/static-asset-caching'
-import fastHead from './fast-head.js'
+import fastHead from './fast-head'
 import fastlyCacheTest from './fastly-cache-test.js'
 import trailingSlashes from './trailing-slashes.js'
 import fastlyBehavior from './fastly-behavior.js'
diff --git a/src/frame/tests/favicons.js b/src/frame/tests/favicons.ts
similarity index 94%
rename from src/frame/tests/favicons.js
rename to src/frame/tests/favicons.ts
index 5af409a5a8..030b35fdd1 100644
--- a/src/frame/tests/favicons.js
+++ b/src/frame/tests/favicons.ts
@@ -1,7 +1,7 @@
 import { describe, expect, test, vi } from 'vitest'
 
-import { SURROGATE_ENUMS } from '#src/frame/middleware/set-fastly-surrogate-key.js'
-import { get } from '#src/tests/helpers/e2etest.js'
+import { SURROGATE_ENUMS } from '@/frame/middleware/set-fastly-surrogate-key.js'
+import { get } from '@/tests/helpers/e2etest.js'
 
 describe('favicon assets', () => {
   vi.setConfig({ testTimeout: 60 * 1000 })
diff --git a/src/learning-track/middleware/learning-track.js b/src/learning-track/middleware/learning-track.ts
similarity index 64%
rename from src/learning-track/middleware/learning-track.js
rename to src/learning-track/middleware/learning-track.ts
index 2f5a5b6e7d..823f4e8c8d 100644
--- a/src/learning-track/middleware/learning-track.js
+++ b/src/learning-track/middleware/learning-track.ts
@@ -1,25 +1,48 @@
-import { getPathWithoutLanguage, getPathWithoutVersion } from '#src/frame/lib/path-utils.js'
-import getLinkData from '../lib/get-link-data.js'
-import { renderContent } from '#src/content-render/index.js'
-import { getDeepDataByLanguage } from '#src/data-directory/lib/get-data.js'
+import type { Response, NextFunction } from 'express'
+
+import type {
+  Context,
+  ExtendedRequest,
+  LearningTrack,
+  LearningTracks,
+  TrackGuide,
+  Page,
+} from '@/types'
+import { getPathWithoutLanguage, getPathWithoutVersion } from '@/frame/lib/path-utils.js'
+import getLinkData from '../lib/get-link-data.js'
+import { renderContent } from '@/content-render/index.js'
+import { getDeepDataByLanguage } from '@/data-directory/lib/get-data.js'
+
+export default async function learningTrack(
+  req: ExtendedRequest,
+  res: Response,
+  next: NextFunction,
+) {
+  if (!req.context) throw new Error('request is not contextualized')
 
-export default async function learningTrack(req, res, next) {
   const noTrack = () => {
-    req.context.currentLearningTrack = {}
+    req.context!.currentLearningTrack = null
     return next()
   }
 
   if (!req.context.page) return next()
 
-  const trackName = req.query.learn
-  if (!trackName) return noTrack()
+  if (!req.query.learn) return noTrack()
+  if (Array.isArray(req.query.learn)) return noTrack()
+  const trackName = req.query.learn as string
 
-  let trackProduct = req.context.currentProduct
-  const allLearningTracks = getDeepDataByLanguage('learning-tracks', req.language)
-  if (req.langauge !== 'en') {
+  let trackProduct = req.context.currentProduct as string
+  // TODO: Once getDeepDataByLanguage is ported to TS
+  // a more appropriate API would be to use `getDeepDataByLanguage<LearningTracks)(...)`
+  const allLearningTracks = getDeepDataByLanguage('learning-tracks', req.language) as LearningTracks
+
+  if (req.language !== 'en') {
     // Don't trust the `.guides` from the translation. It too often has
     // broken Liquid (e.g. `{% ifversion fpt 또는 ghec 또는 ghes %}`)
-    const allEnglishLearningTracks = getDeepDataByLanguage('learning-tracks', 'en')
+    const allEnglishLearningTracks = getDeepDataByLanguage(
+      'learning-tracks',
+      'en',
+    ) as LearningTracks
     for (const [key, tracks] of Object.entries(allLearningTracks)) {
       if (!(key in allEnglishLearningTracks)) {
         // This can happen when the translation of
@@ -47,7 +70,12 @@ export default async function learningTrack(req, res, next) {
   // the case where a learning track has guide paths for a different product
   // than the current learning track product.
   if (!tracksPerProduct) {
-    trackProduct = req.query.learnProduct
+    if (!req.query.learnProduct) return noTrack()
+    if (Array.isArray(req.query.learnProduct)) {
+      trackProduct = req.query.learnProduct[0] as string
+    } else {
+      trackProduct = req.query.learnProduct as string
+    }
     tracksPerProduct = allLearningTracks[trackProduct]
   }
   if (!tracksPerProduct) return noTrack()
@@ -57,14 +85,14 @@ export default async function learningTrack(req, res, next) {
 
   // The trackTitle comes from a data .yml file and may use Liquid templating, so we need to render it
   const renderOpts = { textOnly: true }
-  const trackTitle = await renderContent(track.title, req.context, renderOpts)
+  const trackTitle = (await renderContent(track.title, req.context, renderOpts)) as string
 
-  const currentLearningTrack = { trackName, trackProduct, trackTitle }
+  const currentLearningTrack: LearningTrack = { trackName, trackProduct, trackTitle }
   const guidePath = getPathWithoutLanguage(getPathWithoutVersion(req.pagePath))
 
   // The raw track.guides will return all guide paths, need to use getLinkData
   // so we only get guides available in the current version
-  const trackGuides = await getLinkData(track.guides, req.context)
+  const trackGuides = (await getLinkData(track.guides, req.context)) as TrackGuide[]
 
   const trackGuidePaths = trackGuides.map((guide) => {
     return getPathWithoutLanguage(getPathWithoutVersion(guide.href))
@@ -97,8 +125,13 @@ export default async function learningTrack(req, res, next) {
 
   if (guideIndex > 0) {
     const prevGuidePath = trackGuidePaths[guideIndex - 1]
-    const result = await getLinkData(prevGuidePath, req.context, { title: true, intro: false })
-    if (!result) return noTrack()
+    const resultData = await getLinkData(prevGuidePath, req.context, {
+      title: true,
+      intro: false,
+      fullTitle: false,
+    })
+    if (!resultData) return noTrack()
+    const result = resultData as { href: string; page: Page; title: string }
 
     const href = result.href
     const title = result.title
@@ -107,8 +140,13 @@ export default async function learningTrack(req, res, next) {
 
   if (guideIndex < trackGuidePaths.length - 1) {
     const nextGuidePath = trackGuidePaths[guideIndex + 1]
-    const result = await getLinkData(nextGuidePath, req.context, { title: true, intro: false })
-    if (!result) return noTrack()
+    const resultData = await getLinkData(nextGuidePath, req.context, {
+      title: true,
+      intro: false,
+      fullTitle: false,
+    })
+    if (!resultData) return noTrack()
+    const result = resultData as { href: string; page: Page; title: string }
 
     const href = result.href
     const title = result.title
@@ -123,7 +161,11 @@ export default async function learningTrack(req, res, next) {
 
 // Find the index of a learning track guide path in an array of guide paths,
 // return -1 if not found.
-async function indexOfLearningTrackGuide(trackGuidePaths, guidePath, context) {
+async function indexOfLearningTrackGuide(
+  trackGuidePaths: string[],
+  guidePath: string,
+  context: Context,
+) {
   let guideIndex = -1
 
   for (let i = 0; i < trackGuidePaths.length; i++) {
diff --git a/src/learning-track/tests/lint-data.js b/src/learning-track/tests/lint-data.ts
similarity index 77%
rename from src/learning-track/tests/lint-data.js
rename to src/learning-track/tests/lint-data.ts
index 6451a33946..3e1e3cafb1 100644
--- a/src/learning-track/tests/lint-data.js
+++ b/src/learning-track/tests/lint-data.ts
@@ -1,16 +1,19 @@
 import { describe, expect, test } from 'vitest'
 
-import { loadPages, loadPageMap } from '#src/frame/lib/page-data.js'
-import loadRedirects from '#src/redirects/lib/precompile.js'
-import { getDeepDataByLanguage } from '#src/data-directory/lib/get-data.js'
-import { checkURL } from '#src/tests/helpers/check-url.js'
+import type { LearningTracks } from '@/types'
+import { loadPages, loadPageMap } from '@/frame/lib/page-data.js'
+import loadRedirects from '@/redirects/lib/precompile.js'
+import { getDeepDataByLanguage } from '@/data-directory/lib/get-data.js'
+import { checkURL } from '@/tests/helpers/check-url.js'
 
 const pageList = await loadPages(undefined, ['en'])
 const pages = await loadPageMap(pageList)
 const redirects = await loadRedirects(pageList)
 
 describe('learning tracks', () => {
-  const allLearningTracks = getDeepDataByLanguage('learning-tracks', 'en')
+  // TODO: Once getDeepDataByLanguage is ported to TS
+  // a more appropriate API would be to use `getDeepDataByLanguage<LearningTracks)(...)`
+  const allLearningTracks = getDeepDataByLanguage('learning-tracks', 'en') as LearningTracks
   const topLevels = Object.keys(allLearningTracks)
 
   test.each(topLevels)('learning-track in data/learning-tracks/%s.yml', (topLevel) => {
@@ -33,6 +36,12 @@ describe('learning tracks', () => {
       expect(length, errorMessage).toEqual(size)
     }
 
+    type Trouble = {
+      uri: string
+      index: number
+      redirects: string | undefined
+    }
+    type TroubleTuple = [string, Trouble[]]
     const troubles = Object.entries(learningTracks)
       .map(([learningTrackKey, learningTrack]) => {
         return [
@@ -42,7 +51,7 @@ describe('learning tracks', () => {
             .filter(Boolean),
         ]
       })
-      .filter(([, trouble]) => trouble.length > 0)
+      .filter(([, trouble]) => trouble.length > 0) as TroubleTuple[]
 
     let errorMessage = `In data/learning-tracks/${topLevel}.yml there are ${troubles.length} guides that are not correct.\n`
     let fixables = 0
diff --git a/src/types.ts b/src/types.ts
index f0459077bf..684a5e717c 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -159,6 +159,39 @@ export type Context = {
   productUserExamples?: ProductExample[]
   productGroups?: ProductGroup[]
   featuredLinks?: FeaturedLinksExpanded
+  currentLearningTrack?: LearningTrack | null
+}
+export type LearningTracks = {
+  [group: string]: {
+    [track: string]: {
+      title: string
+      description: string
+      versions?: FrontmatterVersions
+      guides: string[]
+    }
+  }
+}
+export type LearningTrack = {
+  trackName: string
+  trackProduct: string
+  trackTitle: string
+  numberOfGuides?: number
+  currentGuideIndex?: number
+  nextGuide?: {
+    href: string
+    title: string
+  }
+  prevGuide?: {
+    href: string
+    title: string
+  }
+}
+
+export type TrackGuide = {
+  href: string
+  page: Page
+  title: string
+  intro: string
 }
 
 export type FeaturedLinkExpanded = {
@@ -311,6 +344,7 @@ export type Page = {
   earlyAccessToc?: boolean
   autogenerated?: string
   featuredLinks?: FeaturedLinksExpanded
+  redirect_from?: string[]
 }
 
 type ChangeLog = {