diff --git a/.github/workflows/docs-freshness-check.yml b/.github/workflows/docs-freshness-check.yml
new file mode 100644
index 0000000000..09d5cd9beb
--- /dev/null
+++ b/.github/workflows/docs-freshness-check.yml
@@ -0,0 +1,36 @@
+# Checks for outdated documentation content and sends notification about it
+name: Docs Freshness Check
+on: 
+  schedule:
+    - cron: '0 0 1 * *' # once a month
+
+jobs:
+  freshness-check:
+    runs-on: ubuntu-latest
+    env:
+      GH_TOKEN: ${{ secrets.REFERENCE_PAT }}
+      LINEAR_API_KEY: ${{ secrets.LINEAR_API_KEY }}
+    steps:
+      - name: Cancel Previous Runs
+        uses: styfle/cancel-workflow-action@0.9.1
+        with:
+          access_token: ${{ github.token }}
+
+      - name: Checkout
+        uses: actions/checkout@v2.3.5
+        with:
+          fetch-depth: 0
+
+      - name: Setup Node.js environment
+        uses: actions/setup-node@v2.4.1
+        with:
+          node-version: "14"
+          cache: "yarn"
+
+      - name: Install dependencies
+        uses: ./.github/actions/cache-deps
+        with:
+          extension: docs-freshness-check
+
+      - name: Perform Freshness Check
+        run: yarn check:freshness
\ No newline at end of file
diff --git a/package.json b/package.json
index 35899d1079..5f7c327575 100644
--- a/package.json
+++ b/package.json
@@ -70,11 +70,13 @@
     "generate:js-client": "typedoc --options typedoc.js-client.js",
     "generate:entities": "typedoc --options typedoc.entities.js",
     "release:snapshot": "changeset publish --no-git-tags --snapshot --tag snapshot",
-    "generate:announcement": "node ./scripts/doc-change-release.js"
+    "generate:announcement": "node ./scripts/doc-change-release.js",
+    "check:freshness": "node ./scripts/freshness-check.js"
   },
   "dependencies": {
     "@changesets/changelog-github": "^0.4.5",
     "@changesets/cli": "^2.23.0",
+    "@linear/sdk": "^1.22.0",
     "@octokit/core": "^4.0.5",
     "global": "^4.4.0",
     "import-from": "^3.0.0",
diff --git a/scripts/freshness-check.js b/scripts/freshness-check.js
new file mode 100644
index 0000000000..92ddb60be9
--- /dev/null
+++ b/scripts/freshness-check.js
@@ -0,0 +1,154 @@
+#!/usr/bin/env node
+
+const { LinearClient } = require("@linear/sdk");
+const { Octokit } = require("@octokit/core");
+const fs = require('fs');
+const path = require('path');
+
+const octokit = new Octokit({
+  auth: process.env.GH_TOKEN
+});
+
+const linearClient = new LinearClient({
+  apiKey: process.env.LINEAR_API_KEY
+});
+
+const repoPath = path.join('docs', 'content');
+let freshnessCheckLabelId = "";
+let documentationTeamId = "";
+
+async function scanDirectory (startPath) {
+  const files = fs.readdirSync(path.join(startPath), {
+    withFileTypes: true
+  });
+
+  for (const file of files) {
+    const filePath = path.join(startPath, file.name);
+    if (file.isDirectory()) {
+      //if it's references directory, skip
+      if (file.name !== 'references' && file.name !== 'upgrade-guides') {
+        await scanDirectory(filePath);
+      }
+      continue;
+    }
+
+    //check that the file is a markdown file
+    if (file.name.indexOf('.md') === -1 && file.name.indexOf('.mdx') === -1 ) {
+      continue;
+    }
+
+    //if it is a file, check its commits in GitHub
+    const commitResponse = await octokit.request('GET /repos/{owner}/{repo}/commits', {
+      owner: 'medusajs',
+      repo: 'medusa',
+      path: filePath,
+      per_page: 1
+    })
+
+    if (!commitResponse.data.length) {
+      continue;
+    }
+
+    const today = new Date();
+    const lastEditedDate = new Date(commitResponse.data[0].commit.committer.date);
+    const monthsSinceEdited = getMonthDifference(lastEditedDate, today);
+    
+    if (monthsSinceEdited > 6) {
+      //file was edited more than 6 months ago.
+      //check if there's an issue created for this file since the commit date
+      const existingIssue = await linearClient.issues({
+        filter: {
+          createdAt: {
+            gte: subtractMonths(monthsSinceEdited - 6, today)
+          },
+          title: {
+            containsIgnoreCase: `Freshness check for ${filePath}`
+          },
+          labels: {
+            some: {
+              id: {
+                eq: freshnessCheckLabelId
+              }
+            }
+          }
+        },
+        first: 1
+      });
+
+      if (existingIssue.nodes.length) {
+        //an issue has been created for the past 6 months. Don't create an issue for it.
+        continue;
+      }
+
+      console.log(`Creating an issue for ${filePath}...`);
+
+      //there are no issues in the past 6 months. Create an issue
+      await linearClient.issueCreate({
+        teamId: documentationTeamId,
+        title: `Freshness check for ${filePath}`,
+        labelIds: [
+          freshnessCheckLabelId
+        ],
+        description: `File \`${filePath}\` was last edited on ${lastEditedDate.toDateString()}.`
+      })
+    }
+  }
+}
+
+async function main () {
+  //fetch documentation team ID from linear
+  const documentationTeam = await linearClient.teams({
+    filter: {
+      name: {
+        eqIgnoreCase: 'Documentation'
+      }
+    },
+    first: 1
+  });
+
+  if (!documentationTeam.nodes.length) {
+    console.log("Please add Documentation team in Linear first then try again");
+    process.exit(1);
+  }
+
+  documentationTeamId = documentationTeam.nodes[0].id;
+
+  //fetch freshness check label ID from linear
+  const freshnessCheckLabel = await linearClient.issueLabels({
+    filter: {
+      name: {
+        eqIgnoreCase: 'type: freshness-check'
+      },
+      team: {
+        id: {
+          eq: documentationTeamId
+        }
+      }
+    }
+  });
+
+  if (!freshnessCheckLabel.nodes.length) {
+    console.log("Please add freshness check label in Linear under the documentation team first then try again");
+    process.exit(1);
+  }
+
+  freshnessCheckLabelId = freshnessCheckLabel.nodes[0].id;
+
+  await scanDirectory(repoPath);
+}
+
+function getMonthDifference(startDate, endDate) {
+  return (
+    endDate.getMonth() -
+    startDate.getMonth() +
+    12 * (endDate.getFullYear() - startDate.getFullYear())
+  );
+}
+
+function subtractMonths(numOfMonths, date = new Date()) {
+  date.setMonth(date.getMonth() - numOfMonths);
+
+  return date;
+}
+
+main()
\ No newline at end of file
diff --git a/yarn.lock b/yarn.lock
index 6a42491f1e..a78475075c 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2891,6 +2891,15 @@ __metadata:
   languageName: node
   linkType: hard
 
+"@graphql-typed-document-node/core@npm:^3.1.0":
+  version: 3.1.1
+  resolution: "@graphql-typed-document-node/core@npm:3.1.1"
+  peerDependencies:
+    graphql: ^0.8.0 || ^0.9.0 || ^0.10.0 || ^0.11.0 || ^0.12.0 || ^0.13.0 || ^14.0.0 || ^15.0.0 || ^16.0.0
+  checksum: c186e5adceb0dfdaa770856d2f17c831a474f5927d79f984326ecb3d8680ba3c1ee2314f7def1d863692cd9cbe4dffc8bb52fc74ee0aa9b31e9491f24ef59f90
+  languageName: node
+  linkType: hard
+
 "@hapi/address@npm:^2.1.2":
   version: 2.1.4
   resolution: "@hapi/address@npm:2.1.4"
@@ -4165,6 +4174,17 @@ __metadata:
   languageName: node
   linkType: hard
 
+"@linear/sdk@npm:^1.22.0":
+  version: 1.22.0
+  resolution: "@linear/sdk@npm:1.22.0"
+  dependencies:
+    "@graphql-typed-document-node/core": ^3.1.0
+    graphql: ^15.4.0
+    isomorphic-unfetch: ^3.1.0
+  checksum: 7e8f24f617631d027fd606334a498b04014d4c33603bcb3e08073d14f86260d116597983567f8bc147a935e4557180158175b52b9a9a8a270a234b946894a82b
+  languageName: node
+  linkType: hard
+
 "@lmdb/lmdb-darwin-arm64@npm:2.5.2":
   version: 2.5.2
   resolution: "@lmdb/lmdb-darwin-arm64@npm:2.5.2"
@@ -18218,7 +18238,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"graphql@npm:^15.5.1, graphql@npm:^15.7.2":
+"graphql@npm:^15.4.0, graphql@npm:^15.5.1, graphql@npm:^15.7.2":
   version: 15.8.0
   resolution: "graphql@npm:15.8.0"
   checksum: 30cc09b77170a9d1ed68e4c017ec8c5265f69501c96e4f34f8f6613f39a886c96dd9853eac925f212566ed651736334c8fe24ceae6c44e8d7625c95c3009a801
@@ -30050,6 +30070,7 @@ __metadata:
     "@babel/runtime": ^7.11.2
     "@changesets/changelog-github": ^0.4.5
     "@changesets/cli": ^2.23.0
+    "@linear/sdk": ^1.22.0
     "@octokit/core": ^4.0.5
     "@redocly/cli": latest
     "@typescript-eslint/eslint-plugin": ^5.36.2