Yes, you can migrate multiple OLM files to Office 365 simultaneously using the CloudXena OLM to Office 365 Migration Tool. I had several archived OLM files from different employees, and manually importing them one by one would have taken days. This software solved the issue with its batch migration feature. I added all the OLM files into the tool in a single step, connected my Office 365 account, and started the migration process. The software imported emails, contacts, calendars, tasks, and attachments from every OLM file without any file size restrictions. Even large mailbox data is transferred properly without affecting the original structure. One feature I found especially helpful was duplicate removal. Since some mailbox data overlapped between archives, the tool automatically detected duplicate emails based on sender, subject, body, and recipient details. This kept the Office 365 mailbox clean after migration. The software also allows folder-level selection, which means you can migrate only the required folders instead of the entire mailbox. The preview feature helped verify all data before starting the transfer. Overall, if you are handling multiple Outlook for Mac mailboxes and need a reliable batch migration solution, this tool makes the process much faster and easier.
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