I have encountered serval issues of late with trying to migrate a “old” os to a new machine running MacOS 26. The old softwares vary from Big Sur, Monterey and Ventura. The software program allows connects either via Thunderbolt 2/3 wifi (very slow) and ethernet. The issue at hand is the software seems too old to do the transfer it just hangs on the building the database. If you try a later version it seems to kick in and the transfer is done with very little easy.
In the past I have had this issue with legacy macOS and the only way round it was to jump the old machine to a test machine that has a newer macOS.
xBig Sur and Monterey Migrate to Venture or Sonoma ideally.
Catalina migrate to Ventura or Monterey then to Sonoma then you should be good to upgrade to the latest macOS
Migration Chart Guide
| Old Machine macOS | Migrate to |
| High Sierra or below | Catalina |
| Mojave | Monterey |
| Catalina | Monterey |
| Big Sur | Ventura |
| Monterey | Ventura |
| Ventura | Sequoia/Tahoe |
| Sonoma | Tahoe |
| Sequoia | Tahoe |
When Is Migration Assistance Less Necessary?
For casual users with straightforward needs (e.g., syncing photos or documents), Apple’s built-in tools (like iCloud Drive’s drag-and-drop or the “Move to iOS” app) may suffice. However, for:
- Businesses
- Power Users with Large Datasets
- Those Migrating from Non-Apple Systems …professional assistance remains a critical safeguard.
Apple’s Role in Migration Assistance (2026)
Apple likely offers:
- Guided Migration Tools: Step-by-step wizards for transferring data from competitors (e.g., Google, Microsoft) to iCloud.
- Genius Bar & Support: In-person/remote help for complex cases.
- Developer APIs: For third-party migration tools to integrate with Apple’s ecosystem.
Final Verdict
Migration assistance is still highly useful in Apple’s cloud-dominated world, especially for users with complex needs. While automation covers the basics, human expertise ensures reliability, security, and optimization—making it a worthwhile investment for many.