diff --git a/data/glossaries/external.yml b/data/glossaries/external.yml
index f495c0316e..2b3295b411 100644
--- a/data/glossaries/external.yml
+++ b/data/glossaries/external.yml
@@ -37,7 +37,7 @@
 - term: bio
   description: >-
     The user-generated description found on a profile:
-    https://help.github.com/articles/adding-a-bio-to-your-profile/
+    [Adding a bio to your profile](/articles/adding-a-bio-to-your-profile)
 - term: billing cycle
   description: The interval of time for your specific billing plan.
 - term: billing email
@@ -160,8 +160,8 @@
 - term: contributions
   description: >-
     Specific activities on GitHub that will:
-    - Add a square to a user's contribution graph: "[What counts as a contribution](https://help.github.com/articles/viewing-contributions-on-your-profile/#what-counts-as-a-contribution)"
-    - Add activities to a user's timeline on their profile: "[Contribution activity](https://help.github.com/articles/viewing-contributions-on-your-profile/#contribution-activity)"
+    - Add a square to a user's contribution graph: "[What counts as a contribution](/articles/viewing-contributions-on-your-profile/#what-counts-as-a-contribution)"
+    - Add activities to a user's timeline on their profile: "[Contribution activity](/articles/viewing-contributions-on-your-profile/#contribution-activity)"
 - term: contributor
   description: >-
     A contributor is someone who does not have collaborator access to a repository but has contributed to a project and had a pull request they opened merged into the repository.
@@ -230,7 +230,7 @@
   description: >-
     A branch used to experiment with a new feature or fix an issue that is not in production. Also called a topic branch.
 - term: fenced code block
-  description: An indented block of code you can create with GitHub Flavored Markdown using triple backticks \`\`\` before and after the code block. See this [example](https://help.github.com/en/articles/creating-and-highlighting-code-blocks#fenced-code-blocks).
+  description: An indented block of code you can create with GitHub Flavored Markdown using triple backticks \`\`\` before and after the code block. See this [example](/articles/creating-and-highlighting-code-blocks#fenced-code-blocks).
 - term: fetch
   description: >-
     When you use `git fetch`, you're adding changes from the remote repository to
diff --git a/tests/content/lint-files.js b/tests/content/lint-files.js
index 757e4b2c46..e58a587c03 100644
--- a/tests/content/lint-files.js
+++ b/tests/content/lint-files.js
@@ -17,6 +17,7 @@ const rootDir = path.join(__dirname, '../..')
 const contentDir = path.join(rootDir, 'content')
 const reusablesDir = path.join(rootDir, 'data/reusables')
 const variablesDir = path.join(rootDir, 'data/variables')
+const glossariesDir = path.join(rootDir, 'data/glossaries')
 
 const languageCodes = Object.keys(languages)
 
@@ -320,7 +321,19 @@ describe('lint-files', () => {
   const variableYamlRelPaths = variableYamlAbsPaths.map(p => slash(path.relative(rootDir, p)))
   const variableYamlTuples = zip(variableYamlRelPaths, variableYamlAbsPaths)
 
-  describe.each(variableYamlTuples)(
+  const glossariesYamlAbsPaths = walk(glossariesDir, yamlWalkOptions).sort()
+  const glossariesYamlRelPaths = glossariesYamlAbsPaths.map(p => slash(path.relative(rootDir, p)))
+  const glossariesYamlTuples = zip(glossariesYamlRelPaths, glossariesYamlAbsPaths)
+
+  // Returns `content` if its a string, or `content.description` if it can.
+  // Used for getting the nested `description` key in glossary files.
+  function getContent (content) {
+    if (typeof content === 'string') return content
+    if (typeof content.description === 'string') return content.description
+    return null
+  }
+
+  describe.each([...variableYamlTuples, ...glossariesYamlTuples])(
     'in "%s"',
     (yamlRelPath, yamlAbsPath) => {
       let dictionary, isEarlyAccess
@@ -336,8 +349,9 @@ describe('lint-files', () => {
         const matches = []
 
         for (const [key, content] of Object.entries(dictionary)) {
-          if (typeof content !== 'string') continue
-          const valMatches = (content.match(relativeArticleLinkRegex) || [])
+          const contentStr = getContent(content)
+          if (!contentStr) continue
+          const valMatches = (contentStr.match(relativeArticleLinkRegex) || [])
           if (valMatches.length > 0) {
             matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
           }
@@ -351,8 +365,9 @@ describe('lint-files', () => {
         const matches = []
 
         for (const [key, content] of Object.entries(dictionary)) {
-          if (typeof content !== 'string') continue
-          const valMatches = (content.match(languageLinkRegex) || [])
+          const contentStr = getContent(content)
+          if (!contentStr) continue
+          const valMatches = (contentStr.match(languageLinkRegex) || [])
           if (valMatches.length > 0) {
             matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
           }
@@ -366,8 +381,9 @@ describe('lint-files', () => {
         const matches = []
 
         for (const [key, content] of Object.entries(dictionary)) {
-          if (typeof content !== 'string') continue
-          const valMatches = (content.match(versionLinkRegEx) || [])
+          const contentStr = getContent(content)
+          if (!contentStr) continue
+          const valMatches = (contentStr.match(versionLinkRegEx) || [])
           if (valMatches.length > 0) {
             matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
           }
@@ -381,8 +397,9 @@ describe('lint-files', () => {
         const matches = []
 
         for (const [key, content] of Object.entries(dictionary)) {
-          if (typeof content !== 'string') continue
-          const valMatches = (content.match(domainLinkRegex) || [])
+          const contentStr = getContent(content)
+          if (!contentStr) continue
+          const valMatches = (contentStr.match(domainLinkRegex) || [])
           if (valMatches.length > 0) {
             matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
           }
@@ -398,8 +415,9 @@ describe('lint-files', () => {
           const matches = []
 
           for (const [key, content] of Object.entries(dictionary)) {
-            if (typeof content !== 'string') continue
-            const valMatches = (content.match(earlyAccessLinkRegex) || [])
+            const contentStr = getContent(content)
+            if (!contentStr) continue
+            const valMatches = (contentStr.match(earlyAccessLinkRegex) || [])
             if (valMatches.length > 0) {
               matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
             }
@@ -416,8 +434,9 @@ describe('lint-files', () => {
           const matches = []
 
           for (const [key, content] of Object.entries(dictionary)) {
-            if (typeof content !== 'string') continue
-            const valMatches = (content.match(earlyAccessImageRegex) || [])
+            const contentStr = getContent(content)
+            if (!contentStr) continue
+            const valMatches = (contentStr.match(earlyAccessImageRegex) || [])
             if (valMatches.length > 0) {
               matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
             }
@@ -434,8 +453,9 @@ describe('lint-files', () => {
         const matches = []
 
         for (const [key, content] of Object.entries(dictionary)) {
-          if (typeof content !== 'string') continue
-          const valMatches = (content.match(badEarlyAccessImageRegex) || [])
+          const contentStr = getContent(content)
+          if (!contentStr) continue
+          const valMatches = (contentStr.match(badEarlyAccessImageRegex) || [])
           if (valMatches.length > 0) {
             matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
           }
@@ -449,8 +469,9 @@ describe('lint-files', () => {
         const matches = []
 
         for (const [key, content] of Object.entries(dictionary)) {
-          if (typeof content !== 'string') continue
-          const valMatches = (content.match(oldVariableRegex) || [])
+          const contentStr = getContent(content)
+          if (!contentStr) continue
+          const valMatches = (contentStr.match(oldVariableRegex) || [])
           if (valMatches.length > 0) {
             matches.push(...valMatches.map((match) => {
               const example = match
@@ -468,8 +489,9 @@ describe('lint-files', () => {
         const matches = []
 
         for (const [key, content] of Object.entries(dictionary)) {
-          if (typeof content !== 'string') continue
-          const valMatches = (content.match(oldOcticonRegex) || [])
+          const contentStr = getContent(content)
+          if (!contentStr) continue
+          const valMatches = (contentStr.match(oldOcticonRegex) || [])
           if (valMatches.length > 0) {
             matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
           }
@@ -483,8 +505,9 @@ describe('lint-files', () => {
         const matches = []
 
         for (const [key, content] of Object.entries(dictionary)) {
-          if (typeof content !== 'string') continue
-          const valMatches = (content.match(oldExtendedMarkdownRegex) || [])
+          const contentStr = getContent(content)
+          if (!contentStr) continue
+          const valMatches = (contentStr.match(oldExtendedMarkdownRegex) || [])
           if (valMatches.length > 0) {
             matches.push(...valMatches.map((match) => `Key "${key}": ${match}`))
           }