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I was able to solve this problem completely by creating a new Outlook profile. But there is an issue now with autocomplete, I'll start a new thread for that issue. Thanks

OK thanks for the help.

Yes, the April updates had both Office and Outlook 2010 updates. I uninstalled the Outlook update, did not help. Where do I look to see the Save Drafts time setting? Thanks

And the Outlook version is the version you said is the latest.

Thanks for the tip. I tried saving before sending and that does allow the email to be send correctly. But I'd like to try to see if all updates are installed. So I went in to the Office Account like you suggested, and found one update. But it was just the update that I had uninstalled yesterday...

Thanks for the signature info. Regarding updates, she has Office 2013 Home and Student, and Outlook 2013, but when I looked in Winupdate history, I was seeing updates for Office 2010 and Outlook 2010. I noticed updates for both installed a few days ago. (I uninstalled the Outlook 2010 update...

The new message window appears the same in both instances, it says "Untitled - Message (HTML)"

This only happens in one particular circumstance. My friend likes to open the HP scanner software and select Scan to Email. It then creates a pdf file, opens an Outlook 2013 new message, and the pdf file is attached. She adds the recipient address and some text in the body. But when she sends...

Thanks for the info. I had not thought about using iCloud for the contacts sync. I uploaded my contacts to it successfully. That took some doing, it only seems to want a single V card containing all the contacts. I used an old Gmail account to make the conversion. But it worked well. Thanks...

I was planning to use iTunes. But now you've got me curious. What other sync solutions can you recommend? Thanks

I am setting up my newly acquired iPhone to sync contacts with Outlook, as a backup for the phone. I want the phone contacts (which are only going to be phone numbers, at least initially) to be separate from my existing contacts in Outlook. I don't want my existing Outlook contacts on my phone...

OK thanks. The calendar is not there anymore, just trying to understand how all this works. Thanks

Thanks for the info. When I open the backed up pst file, the calendar does not show what we are looking for. So I suspect it is gone as you say. But I am wondering about something you said in your post. When you say some of the older calendar data may be cached, where would it be cached? Is...

It just occurred to me that we may be trying to do something that can't be done. If her calendar view included someone else's calendar that has been shared to her, was that data ever stored in her pst file? (Her friend had created a calendar on the friend's Apple computer, shared it from...

My friend's Outlook calendar got badly messed up and we need to view to calendar on the backup pst that was made a week ago. I've opened the backup pst file, but I am not sure how to get Outlook to display the calendar that is in the backup. Do I need to make the backup pst the default data...

OK thanks for the info.

I am not familiar with app passwords. I've just been reading about them now that you have mentioned it. Is an app password only applicable if two factor authentication is enabled? And is the app password entered into Outlook in place of the Gmail password, and left there permanently? Thanks

This is the Gmail setting that I now suspect could be the issue based on the searching I've been doing. My friend says she already set it to allow less secure applications, which is what Gmail apparently considers Outlook. I have not connected back yet to find out if this is the issue...

Thanks, but those settings I already tried, did not work. I suspect the problem is related to the setting to allow less secure applications.

Yes, that is how I did it when I did a manual configuration. It did not work for me. I also tried port 465, and I also tried non SSL ports, none would work. Thanks