diff --git a/.github/workflows/update-changelog.yml b/.github/workflows/update-changelog.yml
new file mode 100644
index 0000000000..7e9a584f21
--- /dev/null
+++ b/.github/workflows/update-changelog.yml
@@ -0,0 +1,33 @@
+name: Update CHANGELOG
+on:
+  workflow_dispatch
+
+schedule:
+  # Runs every Tuesday at 9 PM Pacific Time (5 AM UTC Wednesday)
+  - cron: '0 5 * * 3'
+
+permissions:
+  contents: write
+  pull-requests: write
+
+jobs:
+  update-changelog:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Check out
+        uses: actions/checkout@v2
+      - name: Install NodeJS
+        uses: actions/setup-node@v4
+        with:
+          node-version: '20.x'
+      - name: Install dependencies
+        run: npm ci
+      - name: Update version.json
+        run: npx gulp updateChangelog
+      - name: Create version update PR
+        uses: peter-evans/create-pull-request@v4
+        with:
+          token: ${{ secrets.GITHUB_TOKEN }}
+          commit-message: Update ${{ github.ref_name }} CHANGELOG
+          title: '[automated] Update ${{ github.ref_name }} CHANGELOG'
+          branch: merge/update-${{ github.ref_name }}-changelog
diff --git a/tasks/gitTasks.ts b/tasks/gitTasks.ts
index 9230729e2e..5f52050639 100644
--- a/tasks/gitTasks.ts
+++ b/tasks/gitTasks.ts
@@ -5,6 +5,7 @@
 
 import { spawnSync } from 'child_process';
 import { Octokit } from '@octokit/rest';
+import { EOL } from 'os';
 
 /**
  * Execute a git command with optional logging
@@ -146,3 +147,16 @@ export async function createPullRequest(
         return null;
     }
 }
+
+/**
+ * Find all tags that match the given version pattern
+ * @param version The `Major.Minor` version pattern to match
+ * @returns A sorted list of matching tags from oldest to newest
+ */
+export async function findTagsByVersion(version: string): Promise<string[]> {
+    const tagList = await git(['tag', '--list', `v${version}*`, '--sort=creatordate'], false);
+    return tagList
+        .split(EOL)
+        .map((tag) => tag.trim())
+        .filter((tag) => tag.length > 0);
+}
diff --git a/tasks/snapTasks.ts b/tasks/snapTasks.ts
index 4579910b18..b284d2cb03 100644
--- a/tasks/snapTasks.ts
+++ b/tasks/snapTasks.ts
@@ -7,6 +7,18 @@ import * as gulp from 'gulp';
 import * as fs from 'fs';
 import * as path from 'path';
 import * as os from 'os';
+import { exec } from 'child_process';
+import { promisify } from 'util';
+import { findTagsByVersion } from './gitTasks';
+
+const execAsync = promisify(exec);
+
+function logWarning(message: string, error?: unknown): void {
+    console.log(`##vso[task.logissue type=warning]${message}`);
+    if (error instanceof Error && error.stack) {
+        console.log(`##[debug]${error.stack}`);
+    }
+}
 
 gulp.task('incrementVersion', async (): Promise<void> => {
     // Get the current version from version.json
@@ -64,3 +76,113 @@ gulp.task('incrementVersion', async (): Promise<void> => {
     changelogLines.splice(lineToInsertAt, 0, ...linesToInsert);
     fs.writeFileSync(changelogPath, changelogLines.join(os.EOL));
 });
+
+gulp.task('updateChangelog', async (): Promise<void> => {
+    // Add a new changelog section for the new version.
+    console.log('Determining version from CHANGELOG');
+
+    const changelogPath = path.join(path.resolve(__dirname, '..'), 'CHANGELOG.md');
+    const changelogContent = fs.readFileSync(changelogPath, 'utf8');
+    const changelogLines = changelogContent.split(os.EOL);
+
+    // Find all the headers in the changelog (and their line numbers)
+    const [currentHeaderLine, currentVersion] = findNextVersionHeaderLine(changelogLines);
+    if (currentHeaderLine === -1) {
+        throw new Error('Could not find the current header in the CHANGELOG');
+    }
+
+    console.log(`Adding PRs for ${currentVersion} to CHANGELOG`);
+
+    const [previousHeaderLine, previousVersion] = findNextVersionHeaderLine(changelogLines, currentHeaderLine + 1);
+    if (previousHeaderLine === -1) {
+        throw new Error('Could not find the previous header in the CHANGELOG');
+    }
+
+    const presentPrIds = getPrIdsBetweenHeaders(changelogLines, currentHeaderLine, previousHeaderLine);
+    console.log(`PRs [#${presentPrIds.join(', #')}] already in the CHANGELOG`);
+
+    const versionTags = await findTagsByVersion(previousVersion!);
+    if (versionTags.length === 0) {
+        throw new Error(`Could not find any tags for version ${previousVersion}`);
+    }
+
+    // The last tag is the most recent one created.
+    const versionTag = versionTags.pop();
+    console.log(`Using tag ${versionTag} for previous version ${previousVersion}`);
+
+    console.log(`Generating PR list from ${versionTag} to HEAD`);
+    const currentPrs = await generatePRList(versionTag!, 'HEAD');
+
+    const newPrs = [];
+    for (const pr of currentPrs) {
+        const match = prRegex.exec(pr);
+        if (!match) {
+            continue;
+        }
+
+        const prId = match[1];
+        if (presentPrIds.includes(prId)) {
+            console.log(`PR #${prId} is already present in the CHANGELOG`);
+            continue;
+        }
+
+        console.log(`Adding new PR to CHANGELOG: ${pr}`);
+        newPrs.push(pr);
+    }
+
+    if (newPrs.length === 0) {
+        console.log('No new PRs to add to the CHANGELOG');
+        return;
+    }
+
+    console.log(`Writing ${newPrs.length} new PRs to the CHANGELOG`);
+
+    changelogLines.splice(currentHeaderLine + 1, 0, ...newPrs);
+    fs.writeFileSync(changelogPath, changelogLines.join(os.EOL));
+});
+
+const prRegex = /^\*.+\(PR: \[#(\d+)\]\(/g;
+
+function findNextVersionHeaderLine(changelogLines: string[], startLine: number = 0): [number, string] {
+    const headerRegex = /^#\s(\d+\.\d+)\.(x|\d+)$/gm;
+    for (let i = startLine; i < changelogLines.length; i++) {
+        const line = changelogLines.at(i);
+        const match = headerRegex.exec(line!);
+        if (match) {
+            return [i, match[1]];
+        }
+    }
+    return [-1, ''];
+}
+
+function getPrIdsBetweenHeaders(changelogLines: string[], startLine: number, endLine: number): string[] {
+    const prs: string[] = [];
+    for (let i = startLine; i < endLine; i++) {
+        const line = changelogLines.at(i);
+        const match = prRegex.exec(line!);
+        if (match && match[1]) {
+            prs.push(match[1]);
+        }
+    }
+    return prs;
+}
+
+async function generatePRList(startSHA: string, endSHA: string): Promise<string[]> {
+    try {
+        console.log(`Executing: roslyn-tools pr-finder -s "${startSHA}" -e "${endSHA}" --format o#`);
+        let { stdout } = await execAsync(
+            `roslyn-tools pr-finder -s "${startSHA}" -e "${endSHA}" --format o#`,
+            { maxBuffer: 10 * 1024 * 1024 } // 10MB buffer
+        );
+
+        stdout = stdout.trim();
+        if (stdout.length === 0) {
+            return [];
+        }
+
+        return stdout.split(os.EOL).filter((pr) => pr.length > 0);
+    } catch (error) {
+        logWarning(`PR finder failed: ${error instanceof Error ? error.message : error}`, error);
+        throw error;
+    }
+}