diff --git a/packages/aws-cdk/lib/settings.ts b/packages/aws-cdk/lib/settings.ts
index e24ca92468162..f8a4b0b789dd4 100644
--- a/packages/aws-cdk/lib/settings.ts
+++ b/packages/aws-cdk/lib/settings.ts
@@ -336,7 +336,7 @@ export class Settings {
     const tags: Tag[] = [];
 
     for (const assignment of nonEmptyTags) {
-      const parts = assignment.split('=', 2);
+      const parts = assignment.split(/=(.*)/, 2);
       if (parts.length === 2) {
         debug('CLI argument tags: %s=%s', parts[0], parts[1]);
         tags.push({
diff --git a/packages/aws-cdk/test/settings.test.ts b/packages/aws-cdk/test/settings.test.ts
index 0738febc435c0..fde5c1c74665c 100644
--- a/packages/aws-cdk/test/settings.test.ts
+++ b/packages/aws-cdk/test/settings.test.ts
@@ -1,5 +1,6 @@
 /* eslint-disable import/order */
 import { Command, Context, Settings } from '../lib/settings';
+import { Tag } from '../lib/cdk-toolkit';
 
 test('can delete values from Context object', () => {
   // GIVEN
@@ -81,6 +82,26 @@ test('can parse string context from command line arguments with equals sign in v
   expect(settings2.get(['context']).foo).toEqual( 'bar=');
 });
 
+test('can parse tag values from command line arguments', () => {
+  // GIVEN
+  const settings1 = Settings.fromCommandLineArguments({ tags: ['foo=bar'], _: [Command.DEPLOY] });
+  const settings2 = Settings.fromCommandLineArguments({ tags: ['foo='], _: [Command.DEPLOY] });
+
+  // THEN
+  expect(settings1.get(['tags']).find((tag: Tag) => tag.Key === 'foo').Value).toEqual('bar');
+  expect(settings2.get(['tags']).find((tag: Tag) => tag.Key === 'foo').Value).toEqual('');
+});
+
+test('can parse tag values from command line arguments with equals sign in value', () => {
+  // GIVEN
+  const settings1 = Settings.fromCommandLineArguments({ tags: ['foo==bar='], _: [Command.DEPLOY] });
+  const settings2 = Settings.fromCommandLineArguments({ tags: ['foo=bar='], _: [Command.DEPLOY] });
+
+  // THEN
+  expect(settings1.get(['tags']).find((tag: Tag) => tag.Key === 'foo').Value).toEqual('=bar=');
+  expect(settings2.get(['tags']).find((tag: Tag) => tag.Key === 'foo').Value).toEqual('bar=');
+});
+
 test('bundling stacks defaults to an empty list', () => {
   // GIVEN
   const settings = Settings.fromCommandLineArguments({