tphil - Thanks for providing the Error Overview information, this is as always very helpful.tphil wrote:
--- Error ---
XXXXXX [1000: IMAP] ['imap-mail.outlook.com' (993) SSL: 1] [Smtp: 'smtp-mail.outlook.com' (587) SSL: 2]
Error (Send)

With this information I can say that for this account you are using IMAP, so the Webmail plugin has nothing to do with this account. It was just coincidence that errors cleared for a while after updating the Webmail plugin.
It happens that it is the Outlook (Microsoft) Email Client using IMAP Servers that is having all the issues and is why you are now getting errors again. That specific error is because PP hasn't yet detected that a connection is broken due to the problems with Outlook IMAP Servers so PP still tries to *send* a command which then produces this PP error.
For more information on this you can go HERE for additional details that are updated when new information becomes available.
Btw, there is an alpha version that has had very good results if you're interested (please carefully read post linked here): http://www.esumsoft.com/Forums/viewtopi ... pha#p34151
Addendum: a recent update in the first link posted above by scrolling down to the bottom of the topic (or click HERE to go directly to the post) provides additional information on this alpha version.