Outlook 2016 IMAP Connection Returns All Email but outlook.com does NOT

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Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#1
My outlook.com account connects to my Spectrum (formerly Time-Warner) email account using IMAP. Over the past few weeks, it no longer returns the most recent email messages from my Spectrum account. It does not return any messages after October 10. It used to work fine. I removed the Spectrum connection and re-added it with the same result.


I primarily use Outlook 2016 (through Office 365 Home) with my outlook.com account. Obviously, it returns the same messages that outlook.com returns, missing all messages after October 10. However, if I add my Spectrum email account directly to Outlook 2016 as an IMAP connection, it returns ALL of my Spectrum email messages up to, and including, the most current ones.


How can the Outlook 2016 IMAP connection to my Spectrum email account return all of my Spectrum messages while the outlook.com IMAP connection to this same account only returns the messages through October 10? Both IMAP connections are set up as close as possible to each other (although the selection choices are not quite the same in the two different IMAP settings). I have used outlook.com for years without any issue -- until recently.


This issue has been driving me nuts for weeks. Any help in resolving it would be greatly appreciated. Thank you.
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#2
How can the Outlook 2016 IMAP connection to my Spectrum email account return all of my Spectrum messages while the outlook.com IMAP connection to this same account only returns the messages through October 10?
something changed on oct 10 that is affecting the outlook.com connection.

is the imap server name correct in the connected account settings?
are the messages getting marked as read on another device? (This shouldn't prevent an imap connect from working but could prevent a pop account from downloading new mail)

(although the selection choices are not quite the same in the two different IMAP settings)
what is different?
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#3
Thank you for your response.

<<something changed on oct 10 that is affecting the outlook.com connection. >>
As far as I know (or can tell), nothing changed on October 10.

<<is the imap server name correct in the connected account settings? >>
Yes. I've checked all settings several times.

<<are the messages getting marked as read on another device?>>
No.

<<what is different?>>
The account settings in Outlook 2016 are just a bit different than in outlook.com. The information needed is just organized differently and more thorough in Outlook 2016. They both, of course, ask for the incoming (IMAP) and outgoing (SMTP) server names (which, in my case for Spectrum Cable, both are "mail.twc.com" ) and the ports (for Spectrum, it's 143 for incoming and 587 for outgoing). Outlook.com has a drop-down box for "Authentication" (I'm using "Basic" for Spectrum) while Outlook 2016 has a checkbox for "My outgoing server (SMTP) requires authentication" (which is checked for Spectrum). Outlook.com has a single Encryption dropdown box for the incoming server (which is set to "None" for Spectrum) and no such setting for the outgoing server while Outlook 2016 has a dropdown "Encryption" box for each server (which are both set to "None" for Spectrum). The Outlook 2016 account settings also include a few additional non-essential settings including those for testing the account setup.

Both my Outlook 2016 and outlook.com IMAP account settings are setup identically (at least as far as I can tell). So why is outlook.com only returning the messages on and before October 10. It makes absolutely no sense to me. I am not aware of ANY changes that were made on or about October that might have caused this problem. I have no idea how to troubleshoot this issue. I have spent countless hours and days trying to resolve these issues.

I've used Outlook since the first version was released many years ago and have always liked it very much. But ever since Microsoft went to using Exchange mailboxes for outlook.com, I've been having nothing but problems with it.

I have one more related issue that I just discovered earlier today. I sent a new email message to someone yesterday from Outlook 2016 using the outlook.com-connected account that uses the Exchange mailbox (i.e., "Outlook_<16 letter and digit number)@outlook.com") and I received an undeliverable mail notification: "This message could not be sent. You do not have the permission to send the message on behalf of the specified user.". Do you know why I received this notification... And, more importantly, HOW do I fix it. I'm using Outlook 2016 as part of Outlook 365 Home. I searched the internet for answers but could only find information related to the "business" edition of Outlook 365.

Thank you for your help.
 
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