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It appears this update occurred today. Since the update, Outlook will not automatically bring in email (push setting) and must be manually synced each time. I have found no settings to help fix this. This stopped working concurrently with the update. Please fix this.
Using older versions of Outlook for Mac for personal email and calendar
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I emptied my Outlook cache and that appears to have fixed it. Right click inbox > properties > empty cache
My school is experiencing the same issue - we have hundreds of teachers on Macs using the Legacy version of Outlook because it allows the creation of Contact groups and they are not receiving their email. I could not email them to tell them it was not working so my team is trying to get the message out via face to face networking but we have users spread across 4 islands. This is very problematic. I tried the emptying cache suggestion someone suggested but it did not work. Please fix this as soon as possible.
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I have the same problem....fix please!
I emptied my Outlook cache and that appears to have fixed it. Right click inbox > properties > empty cache
I tried this on a clients computer and it was still giving her syncing issues afterwards. I tried the "Sync Shared Mailboxes" workaround that seems to be working. Email has been auto-syncing for the last 16 hours