outlook.live.com Sent mails not saved in Sent items

You'd think that could be the case. But no, as other posters have advised, they aren't saved to the mailbox of the connected account.  Connected accounts work very smoothly in gmail and are all saved in the gmail folders and not the remote mailbox. Unfortunately, I personally, do not like the layout of gmail otherwise I wouldn't be trying so hard to find a solution to this issue. And Outlook all worked really well until they upgraded it last year.

You would think that with all the complaints about the same issue yhay Microsoft would eventually admit they had a problem with the update and either fix it or revert back to the previous version. I guess that customer support and feelings are not a part of the Microsoft philosophy.

To all of you who have experienced this problem (including me), I have read through all 12 pages of this thread with the same level of frustration.  I have been struggling with this problem since late 2016 and I assume there was some sort of upgrade to Outlook Mail at that time but I honestly don't remember.

Anyway, I have been playing around with different ways to configure the connected account and may have stumbled across a fix.  Let me outline what I did.  I have been running like this for a couple of days and everything seems fine.

• When I originally set up my Microsoft account (let's call this MS Account A) I used my personal email address ******@comcast.net as my login ID.  I never set up a ******@outlook.com email address.  I believe that MS set up one behind the scenes using my Unique ID in some form or fashion.
• I decided to create a new Microsoft account and to use the ******@outlook.com login ID instead.  When I did this I was asked to pick a user name that wasn't already in use (let's call this MS Account B).  The log in address for this account is ******@outlook.com.
• In MS Account B, I set up a new Connected Account between Microsoft and Comcast using the manual set up process instead of the automatic process.  I used the exact same Comcast email that I used with MS Account A.  I set up the connection as a POP instead of an IMAP.  I also set the "Use different name and email address to send email" setting to my Comcast address.
• The immediate result is that when I sent emails from MS Account B the Sent Items folder is keeping track of each email sent and the email recipient sees my Comcast address and not my Outlook address. So far so good.
• Next step for me was to connect multiple devices i.e. Windows Phone, (2) Windows 10 PC, and a Tablet to the MS Account B.  Because I wanted my folders to be synced across all of these devices, I decided to set up these connections as IMAP.  So, the set up looks like this
  • User Devices (4) -->IMAP -->MS Account B -->POP -->Comcast
• Lo and behold, everything works as it should.  Incoming and Sent emails appear in their respective folders and are synced across all devices.

Some caveats about this:

• I have not identified a way to move all of my content from MS Account A to MS Account B, so I have kept both accounts open to get to my historical information.
• This is working with Comcast and I can't vouch for other ISPs or email providers.
• Since the connection between MS Account B and Comcast is POP, the features and functions will not be the same as an IMAP connection would be.
• I didn't try to set up the MS Account B to Comcast connection as IMAP because I think that might be the problem to start with.  Also, I don't want to delete the emails on my Comcast server anyway.  (As an FYI, while experimenting with my MS Account A, I once set it up as an SMTP Only account and it tracked my Sent emails perfectly.  This also leads me to believe that the IMAP setting is the problem.)

Best of luck to all of you with this information.  If it doesn't work for you, don't come after me :>) - I'm just an end-user with too much time on my hands.