Next, An Import & Export Wizard will appear. I think you would then turn on sync and hope your two devices get sync'dīut do make sure you have a backup first as the whole process can be a little tricky. Manual Importing Android Contact Files to Outlook To add contacts from Android to Outlook, proceed with the below-mentioned steps: Run Microsoft Outlook. It's possible that your desktop contacts may also appear in the native Android contacts app and these can be deleted en-masse by selecting each one first then deleting. Tap on this and you can see your contacts (Poeple) but as far as I know you can only delete one at a time. If however you want to delete contacts on the smartphone, within Outlook, then you tap on the search Icon and the word Contacts appears at the top. I've found that syncing between desktop and phone is not an instant process and can take many minutes in some case. So I'm not sure why you would want to clear out the phone Outlook and then re-import as the two should be in sync. If you're deleting or editing contacts on the desktop then those changes should appear on your phone during the sync process and vice versa. If you are going to make changes on a large scale like you want I would suggest exporting all your contacts first as a backup and ensure sync is off. I confess that they whole synchronising process seems a bit flaky to me at times but it works. I have both contacts lists synchronised so that changes on one affect changes on the other plus the contacts also show up in the native Android contacts app. I have a similar setup to you Outlook 365 Desktop and Outlook Android on smartphone.
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