Microsoft Office 365 Migration Gotchas

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Here are some tips to help you with your upcoming Microsoft 365 migration (formerly Office 365):

Know how your user base connects

  • If they are using the Outlook Client, earlier versions are not supported. And even if technically supported by Microsoft, some versions have limitations. Make sure the tool you use can easily identify the Outlook client version BEFORE you cutover your MX records.
  • Do you have a significant number of users working via an RDP Server? Many tools have a hard time automating configuration on the new Outlook 365 profile. You’ll need to build in time to manually configure each profile.
DNS propagation is inconsistent
  • Because the Autodiscover record is so critical for Macs connecting to 365, organizations that have folks connecting from multiple locations sometimes have trouble making that connection to 365 from Outlook soon after the cutover.
  • Mail can still be dropped in the source mailbox for weeks. Make sure you have a tool that continues to sync mail even after the cutover of the MX record.