diff --git a/src/libs/TryNewDotUtils.ts b/src/libs/TryNewDotUtils.ts
index 10e692afa63f..6cfa5a30f26b 100644
--- a/src/libs/TryNewDotUtils.ts
+++ b/src/libs/TryNewDotUtils.ts
@@ -1,11 +1,24 @@
+import {differenceInDays} from 'date-fns';
 import type {OnyxEntry} from 'react-native-onyx';
 import type {TryNewDot} from '@src/types/onyx';
 import {isEmptyObject} from '@src/types/utils/EmptyObject';
 
+const NEW_DOT_MIN_DAYS_BEFORE_HIDING_CLASSIC_REDIRECT = 30;
+
 function isLockedToNewApp(tryNewDot: OnyxEntry<TryNewDot>): boolean {
     return tryNewDot?.isLockedToNewApp === true;
 }
 
+function hasBeenInNewDot30Days(tryNewDot: OnyxEntry<TryNewDot>): boolean {
+    const classicRedirect = tryNewDot?.classicRedirect;
+    if (!classicRedirect || classicRedirect.dismissed !== false || !classicRedirect.timestamp) {
+        return false;
+    }
+
+    const daysSinceNudge = differenceInDays(new Date(), new Date(classicRedirect.timestamp));
+    return daysSinceNudge >= NEW_DOT_MIN_DAYS_BEFORE_HIDING_CLASSIC_REDIRECT;
+}
+
 function shouldBlockOldAppExit(tryNewDot: OnyxEntry<TryNewDot>, isLoadingTryNewDot: boolean, shouldSetNVP: boolean): boolean {
     if (isLockedToNewApp(tryNewDot)) {
         return true;
@@ -15,7 +28,7 @@ function shouldBlockOldAppExit(tryNewDot: OnyxEntry<TryNewDot>, isLoadingTryNewD
 }
 
 function isOldAppRedirectBlocked(tryNewDot: OnyxEntry<TryNewDot>, shouldRespectMobileLock: boolean): boolean {
-    return tryNewDot?.classicRedirect?.isLockedToNewDot === true || (shouldRespectMobileLock && isLockedToNewApp(tryNewDot));
+    return tryNewDot?.classicRedirect?.isLockedToNewDot === true || hasBeenInNewDot30Days(tryNewDot) || (shouldRespectMobileLock && isLockedToNewApp(tryNewDot));
 }
 
 function shouldHideOldAppRedirect(tryNewDot: OnyxEntry<TryNewDot>, isLoadingTryNewDot: boolean, shouldRespectMobileLock: boolean): boolean {
@@ -34,4 +47,4 @@ function shouldUseOldApp(tryNewDot: TryNewDot): boolean | undefined {
     return tryNewDot.classicRedirect.dismissed;
 }
 
-export {isLockedToNewApp, isOldAppRedirectBlocked, shouldBlockOldAppExit, shouldHideOldAppRedirect, shouldUseOldApp};
+export {hasBeenInNewDot30Days, isLockedToNewApp, isOldAppRedirectBlocked, shouldBlockOldAppExit, shouldHideOldAppRedirect, shouldUseOldApp};
diff --git a/tests/unit/TryNewDotUtilsTest.ts b/tests/unit/TryNewDotUtilsTest.ts
index 76b7e20678d7..a2f4244aed33 100644
--- a/tests/unit/TryNewDotUtilsTest.ts
+++ b/tests/unit/TryNewDotUtilsTest.ts
@@ -1,5 +1,6 @@
+import {subDays} from 'date-fns';
 import Onyx from 'react-native-onyx';
-import {isOldAppRedirectBlocked, shouldBlockOldAppExit, shouldHideOldAppRedirect, shouldUseOldApp} from '@src/libs/TryNewDotUtils';
+import {hasBeenInNewDot30Days, isOldAppRedirectBlocked, shouldBlockOldAppExit, shouldHideOldAppRedirect, shouldUseOldApp} from '@src/libs/TryNewDotUtils';
 import ONYXKEYS from '@src/ONYXKEYS';
 import type {TryNewDot} from '@src/types/onyx';
 import waitForBatchedUpdatesWithAct from '../utils/waitForBatchedUpdatesWithAct';
@@ -68,6 +69,71 @@ describe('TryNewDotUtils', () => {
         expect(shouldBlockOldAppExit({isLockedToNewApp: true} as TryNewDot, false, false)).toBe(true);
     });
 
+    it('blocks the OldDot redirect when the classicRedirect nudge has gone stale', () => {
+        const tryNewDot = {
+            classicRedirect: {
+                dismissed: false,
+                timestamp: subDays(new Date(), 31).toISOString(),
+            },
+        } as unknown as TryNewDot;
+
+        expect(isOldAppRedirectBlocked(tryNewDot, false)).toBe(true);
+    });
+
+    it('still shows the OldDot redirect when the classicRedirect nudge is fresh', () => {
+        const tryNewDot = {
+            classicRedirect: {
+                dismissed: false,
+                timestamp: subDays(new Date(), 5).toISOString(),
+            },
+        } as unknown as TryNewDot;
+
+        expect(isOldAppRedirectBlocked(tryNewDot, false)).toBe(false);
+    });
+
+    it('reports that a user has been in NewDot 30 days when the nudge is over a month old and not dismissed', () => {
+        const tryNewDot = {
+            classicRedirect: {
+                dismissed: false,
+                timestamp: subDays(new Date(), 31).toISOString(),
+            },
+        } as unknown as TryNewDot;
+
+        expect(hasBeenInNewDot30Days(tryNewDot)).toBe(true);
+    });
+
+    it('does not report 30 days in NewDot when the nudge is less than a month old', () => {
+        const tryNewDot = {
+            classicRedirect: {
+                dismissed: false,
+                timestamp: subDays(new Date(), 10).toISOString(),
+            },
+        } as unknown as TryNewDot;
+
+        expect(hasBeenInNewDot30Days(tryNewDot)).toBe(false);
+    });
+
+    it('does not report 30 days in NewDot once the user has dismissed the nudge', () => {
+        const tryNewDot = {
+            classicRedirect: {
+                dismissed: true,
+                timestamp: subDays(new Date(), 60).toISOString(),
+            },
+        } as unknown as TryNewDot;
+
+        expect(hasBeenInNewDot30Days(tryNewDot)).toBe(false);
+    });
+
+    it('does not report 30 days in NewDot when no timestamp is set', () => {
+        const tryNewDot = {
+            classicRedirect: {
+                dismissed: false,
+            },
+        } as unknown as TryNewDot;
+
+        expect(hasBeenInNewDot30Days(tryNewDot)).toBe(false);
+    });
+
     it('preserves isLockedToNewApp when nvp_tryNewDot is merged', async () => {
         await Onyx.set(ONYXKEYS.NVP_TRY_NEW_DOT, {
             isLockedToNewApp: true,