Many Sent Item folders

Outlook version
Outlook 2016 64 bit
Email Account
POP3
#1
I have two email services: RoadRunner (main source) and Outlook.com (for syncing)
RoadRunner (RR) shows folders: Sent Items, Sent Messages, and Sent Mail
Sent Items stopped receiving items about 11/13
Sent Messages has a few random outgoing mails up to two weeks ago
Sent Mail is empty
Outlook has a single Sent Items folder that now contains all my sent mail.
This happened unexpectedly about mid-November. Have I missed some “improvement” to Outlook 2016? I also notice orange “flags” on some messages. What do they signify?
Has MS explained these changes? Where should I look for info? Is this a part of Office 2019?
How can I have all my sent mail go to the Sent Items folder under the RR folder group?
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#2
RoadRunner (RR) shows folders: Sent Items, Sent Messages, and Sent Mail
Sent Items
stopped receiving items about 11/13
Sent Messages has a few random outgoing mails up to two weeks ago
Sent Mail is empty
Sent Items is Outlook's doing, iphone creates Sent Messages but Android could too - or it could be the default for the mailbox.. but I suspect the default is the Sent Mail folder (used if you log in and send message).
Outlook has a single Sent Items folder that now contains all my sent mail.
This happened unexpectedly about mid-November. Have I missed some “improvement” to Outlook 2016? I also notice orange “flags” on some messages. What do they signify?
I don't think you've missed anything. Are you sending mail from the outlook address or RR?
 
Outlook version
Outlook 2016 64 bit
Email Account
POP3
#3
Sent Items is Outlook's doing, iphone creates Sent Messages but Android could too - or it could be the default for the mailbox.. but I suspect the default is the Sent Mail folder (used if you log in and send message).

I don't think you've missed anything. Are you sending mail from the outlook address or RR?
Aloha Diane.
I send all my mail from RoadRunner. I'd like to get it back into the RR Sent Items folder.

The RR Sent Items folder stopped showing sent items on the 13th of Nov. for no reason I can understand.
I find all my sent items, older right up to yesterday (including copies of those "left" in the RR folder ) are now in the Outlook Sent Items folder

Sent Items is Outlook's doing, iphone creates Sent Messages but Android could too - or it could be the default for the mailbox.. but I suspect the default is the Sent Mail folder (used if you log in and send message).

I don't think you've missed anything. Are you sending mail from the outlook address or RR?
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#4
I find all my sent items, older right up to yesterday (including copies of those "left" in the RR folder ) are now in the Outlook Sent Items folder
Add the From field to the view and group by it. Then you can drag the RR mail to the correct send folder.

But, unless you to RR up as a connected account in Outlook.com, the sent items should be in the RR folders, where the incoming RR mail goes.
 
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