Moving Our Team from Personal Gmail to Microsoft 365—Why Is IMAP Leaving So Much Behind?

Our company has eight employees, and until now everyone has been using personal Gmail accounts for work. Since we’re moving to Microsoft 365 next week, I thought the migration would be straightforward using Microsoft’s IMAP method. Unfortunately, that’s not what happened. Emails started transferring, but contacts and calendars were completely missing. A few accounts even failed during the migration, forcing us to restart the process. We have years of client conversations, meeting schedules, and contact information, so manually rebuilding everything isn’t really an option. Repeating the same migration steps for every employee is taking far more time than we expected, and with our deadline getting closer, I’m starting to worry we’ll miss something important.

After looking through different IT forums, I found several recommendations for the DRS Softech Gmail Backup Tool. From what I’ve read, it’s designed for personal Gmail accounts as well as larger migration projects and doesn’t rely only on IMAP email transfer. Instead, it can migrate emails, contacts, calendars, attachments, tasks, and notes while maintaining the original mailbox structure and metadata. Features like Preview, Date Filter, Remove Duplicate Emails, and batch processing also seem useful because we don’t need to move every old email. The software also works on both Windows and macOS, which fits our mixed office environment without requiring complicated setup.

Around the time I finished comparing different migration options, I realized that many businesses choose this approach because they need more than basic email transfer. Being able to migrate Gmail to Office 365 without manually exporting contacts and calendars separately would save us a huge amount of time. The option to process multiple accounts together and avoid migration failures sounds much more practical than repeating IMAP imports for every user. Has anyone here migrated personal Gmail accounts rather than Google Workspace? I’d really appreciate hearing what worked best before we commit to one solution.