diff --git a/lib/deprecations.js b/lib/deprecations.js
new file mode 100644
index 00000000..8f198f6e
--- /dev/null
+++ b/lib/deprecations.js
@@ -0,0 +1,57 @@
+'use strict';
+
+const { promises: fs } = require('fs');
+const path = require('path');
+const replace = require('replace-in-file');
+
+const newDeprecationPattern =
+/<\s*a id="DEP0([X]+[0-9]*)+"[^>]*><\s*\/\s*a>/g;
+
+async function getUnmarkedDeprecations() {
+  const deprecationFilePath = path.resolve('doc', 'api', 'deprecations.md');
+  const deprecationFile = await fs.readFile(deprecationFilePath, 'utf8');
+
+  const unmarkedDeprecations = [
+    ...deprecationFile.matchAll(newDeprecationPattern)
+  ].map(m => m[1]);
+
+  return unmarkedDeprecations;
+}
+
+async function updateDeprecations() {
+  const deprecationPattern =
+    /<\s*a id="DEP0([0-9]{3})+"[^>]*><\s*\/\s*a>/g;
+
+  const deprecationFilePath = path.resolve('doc', 'api', 'deprecations.md');
+  const deprecationFile = await fs.readFile(deprecationFilePath, 'utf8');
+
+  const unmarkedDeprecations = await getUnmarkedDeprecations();
+  const deprecationNumbers = [
+    ...deprecationFile.matchAll(deprecationPattern)
+  ].map(m => m[1]).reverse();
+
+  // Pull highest deprecation number off the list and increment from there.
+  let depNumber = parseInt(deprecationNumbers[0]) + 1;
+
+  // Loop through each new unmarked deprecation number and replace instances.
+  for (const unmarked of unmarkedDeprecations) {
+    await replace({
+      files: [
+        'doc/api/*.md',
+        'lib/**/*.js',
+        'src/**/*.{h,cc}',
+        'test/**/*.js'
+      ],
+      ignore: 'test/common/README.md',
+      from: new RegExp(`DEP0${unmarked}`, 'g'),
+      to: `DEP0${depNumber}`
+    });
+
+    depNumber++;
+  }
+}
+
+module.exports = {
+  updateDeprecations,
+  getUnmarkedDeprecations
+};
diff --git a/lib/landing_session.js b/lib/landing_session.js
index 38898c4d..18d0efac 100644
--- a/lib/landing_session.js
+++ b/lib/landing_session.js
@@ -1,14 +1,16 @@
 'use strict';
 
 const path = require('path');
+const {
+  getUnmarkedDeprecations,
+  updateDeprecations
+} = require('./deprecations');
 
 const {
   runAsync, runSync, forceRunAsync
 } = require('./run');
 const Session = require('./session');
-const {
-  shortSha
-} = require('./utils');
+const { shortSha } = require('./utils');
 
 const isWindows = process.platform === 'win32';
 
@@ -84,6 +86,18 @@ class LandingSession extends Session {
         process.exit(1);
       }
     }
+
+    // Update any new deprecations in the codebase.
+    const unmarkedDepCount = await getUnmarkedDeprecations();
+    if (unmarkedDepCount > 0) {
+      cli.startSpinner('Assigning deprecation numbers to DEPOXXX items');
+      const updatedDepCount = await updateDeprecations();
+
+      // Amend the last commit with the updated deprecation items.
+      await runAsync('git', ['commit', '--amend', '--no-edit']);
+      cli.stopSpinner(`Updated ${updatedDepCount} DEPOXXX items in codebase`);
+    }
+
     cli.ok('Patches applied');
     return patch;
   }
diff --git a/lib/prepare_release.js b/lib/prepare_release.js
index 9eec1706..87cc1a66 100644
--- a/lib/prepare_release.js
+++ b/lib/prepare_release.js
@@ -1,13 +1,17 @@
 'use strict';
 
 const path = require('path');
-const fs = require('fs').promises;
+const { promises: fs } = require('fs');
 const semver = require('semver');
 const replace = require('replace-in-file');
 
 const { getMergedConfig } = require('./config');
 const { runAsync, runSync } = require('./run');
 const { writeJson, readJson } = require('./file');
+const {
+  getUnmarkedDeprecations,
+  updateDeprecations
+} = require('./deprecations');
 
 const isWindows = process.platform === 'win32';
 
@@ -113,10 +117,22 @@ class ReleasePreparation {
     await this.updateREPLACEMEs();
     cli.stopSpinner('Updated REPLACEME items in docs');
 
-    // Update any new deprecations in the codebase.
-    cli.startSpinner('Updating DEPOXXX items in codebase');
-    const depCount = await this.updateDeprecations();
-    cli.stopSpinner(`Updated ${depCount} DEPOXXX items in codebase`);
+    // Check for any unmarked deprecations in the codebase.
+    const unmarkedDepCount = await getUnmarkedDeprecations();
+    if (unmarkedDepCount > 0) {
+      const mark = await cli.prompt(
+        `Automatically mark ${unmarkedDepCount} deprecations?`);
+      if (mark) {
+        cli.startSpinner(
+          `Marking ${unmarkedDepCount} unmarked DEPOXXX items in codebase`);
+        const depCount = await updateDeprecations();
+        cli.stopSpinner(`Updated ${depCount} DEPOXXX items in codebase`);
+      } else {
+        await cli.prompt('Finished updating unmarked DEPOXXX items?',
+          { defaultAnswer: false });
+        cli.stopSpinner('Finished updating DEPOXXX items in codebase');
+      }
+    }
 
     // Fetch date to use in release commit & changelogs.
     const todayDate = new Date().toISOString().split('T')[0];
@@ -230,45 +246,6 @@ class ReleasePreparation {
     ]).trim();
   }
 
-  async updateDeprecations() {
-    const deprecationPattern =
-      /<\s*a id="DEP0([0-9]{3})+"[^>]*><\s*\/\s*a>/g;
-    const newDeprecationPattern =
-      /<\s*a id="DEP0([X]+[0-9]*)+"[^>]*><\s*\/\s*a>/g;
-
-    const deprecationFilePath = path.resolve('doc', 'api', 'deprecations.md');
-    const deprecationFile = await fs.readFile(deprecationFilePath, 'utf8');
-
-    const deprecationNumbers = [
-      ...deprecationFile.matchAll(deprecationPattern)
-    ].map(m => m[1]).reverse();
-    const newDeprecationNumbers = [
-      ...deprecationFile.matchAll(newDeprecationPattern)
-    ].map(m => m[1]);
-
-    // Pull highest deprecation number off the list and increment from there.
-    let depNumber = parseInt(deprecationNumbers[0]) + 1;
-
-    // Loop through each new unmarked deprecation number and replace instances.
-    for (const newDep of newDeprecationNumbers) {
-      await replace({
-        files: [
-          'doc/api/*.md',
-          'lib/**/*.js',
-          'src/**/*.{h,cc}',
-          'test/**/*.js'
-        ],
-        ignore: 'test/common/README.md',
-        from: new RegExp(`DEP0${newDep}`, 'g'),
-        to: `DEP0${depNumber}`
-      });
-
-      depNumber++;
-    }
-
-    return newDeprecationNumbers.length;
-  }
-
   async updateREPLACEMEs() {
     const { newVersion } = this;