diff --git a/apps/web/modules/onboarding/store/onboarding-store.ts b/apps/web/modules/onboarding/store/onboarding-store.ts
index c6e045cca4..a45ff0f618 100644
--- a/apps/web/modules/onboarding/store/onboarding-store.ts
+++ b/apps/web/modules/onboarding/store/onboarding-store.ts
@@ -1,8 +1,23 @@
+import type { PersistOptions } from "zustand/middleware";
 import { create } from "zustand";
 import { persist } from "zustand/middleware";
 
 import { onboardingIndexedDBStorage } from "./onboarding-storage";
 
+// Thresholds for detecting oversized images (in characters of base64 string)
+// Images larger than these were uploaded before the cropping fix and should be cleared
+const LOGO_SIZE_THRESHOLD = 500_000; // ~500KB - properly cropped logos are ~50-150KB
+const BANNER_SIZE_THRESHOLD = 1_500_000; // ~1.5MB - properly cropped banners are ~200-500KB
+
+/**
+ * Checks if a base64 image string exceeds the given threshold.
+ * Returns true if the image should be cleared (is oversized).
+ */
+function isOversizedImage(imageData: string | null, threshold: number): boolean {
+  if (!imageData) return false;
+  return imageData.length > threshold;
+}
+
 export type PlanType = "personal" | "team" | "organization";
 export type InviteRole = "MEMBER" | "ADMIN";
 
@@ -189,7 +204,42 @@ export const useOnboardingStore = create<OnboardingState>()(
     {
       name: "cal-onboarding-storage", // Storage key
       storage: onboardingIndexedDBStorage, // Use IndexedDB instead of localStorage for larger capacity
-      // Optional: Only persist certain fields
+      // Version 0: Had issue with Image sizes being too large. 
+      // Version 1: We fixed that and also migrated to version-1 to facilitate one-time cleanup of all oversized images.
+      version: 1,
+      migrate: (persistedState, version) => {
+        if (version >= 1) {
+          return persistedState as OnboardingState;
+        }
+        const state = persistedState as OnboardingState;
+
+        // Migration from version 0 (no version) to version 1:
+        // Clear oversized images that were uploaded before the cropping fix (PR #27285)
+        // These large images cause 429 errors when sent to the server
+        if (state.organizationBrand) {
+          if (isOversizedImage(state.organizationBrand.logo, LOGO_SIZE_THRESHOLD)) {
+            state.organizationBrand.logo = null;
+          }
+          if (isOversizedImage(state.organizationBrand.banner, BANNER_SIZE_THRESHOLD)) {
+            state.organizationBrand.banner = null;
+          }
+        }
+
+        if (state.teamBrand) {
+          if (isOversizedImage(state.teamBrand.logo, LOGO_SIZE_THRESHOLD)) {
+            state.teamBrand.logo = null;
+          }
+        }
+
+        if (state.personalDetails) {
+          if (isOversizedImage(state.personalDetails.avatar, LOGO_SIZE_THRESHOLD)) {
+            state.personalDetails.avatar = null;
+          }
+        }
+
+        return state;
+      },
+      // Only persist certain fields
       partialize: (state) => ({
         selectedPlan: state.selectedPlan,
         organizationDetails: state.organizationDetails,
@@ -204,6 +254,6 @@ export const useOnboardingStore = create<OnboardingState>()(
         teamId: state.teamId,
         personalDetails: state.personalDetails,
       }),
-    }
+    } as PersistOptions<OnboardingState, Partial<OnboardingState>>
   )
 );