Outlook.com IMAP folder replication in Windows Live Mail / Windows 8/1

I have a situation that I'd like to make better.
The user has an account on hotmail / Outlook.com and had been using web mail.
Then she realized that she'd like to use the "send by email" integrated commands in various app's.
That requires an email client running on the computer and won't work with web mail unless the interface is specifically designed to do that.
So, I got Windows Live Mail working on this Windows 8.1 computer and everything set up with an IMAP account for her Outlook.com account.

So far, so good.
The folders appear to sync properly.

But, fairly often there's an error that says in part:
"Your IMAP command could hot be sent to the server due to non-network errors"
and it seems to take a long time to synchronize otherwise unchanged folders.

I don't know where to begin to solve this....
LVL 27
Fred MarshallPrincipalAsked:
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

x
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

JohnBusiness Consultant (Owner)Commented:
Windows Live Mail is not the most reliable mail client there is (I have it on one computer where it use is not critical).

Any chance, then, of using Outlook?  Office 2013 is available quite inexpensively on subscription and works great on Windows 8.1.  You can use the connector for Outlook.com.
0
Fred MarshallPrincipalAuthor Commented:
Yes, I could install any number of email clients for this purpose.  But there's a learning curve issue with the user as well.  So, I'd rather fix what's there.
0
Fred MarshallPrincipalAuthor Commented:
Is Windows Live Mail really flaky?  Or is there hope for it?

The most recent issue is that it reports it can't access the Inbox folder and suggests refreshing the folders - which is driving the user quite mad.

Would you venture into Exchange-based Outlook 2013 / Outlook.com connection on Outlook 2013 if:
- the user is quite inexperienced
- you (I) have no experience with Exchange mail

I don't want to suggest something that's going to take a lot (more) of my chargeable time.

John's comments seem quite good.  How about some confirmation?

Might one use Outlook 2013 and, rather than "connecting" to Outlook.com, simply set up an IMAP account for Outlook.com.  Which is better / less likely to need support?
0
Protecting & Securing Your Critical Data

Considering 93 percent of companies file for bankruptcy within 12 months of a disaster that blocked access to their data for 10 days or more, planning for the worst is just smart business. Learn how Acronis Backup integrates security at every stage

JohnBusiness Consultant (Owner)Commented:
Windows Live Mail is a light duty client and any effort to push it results in reliability errors. I would avoid it if you can.

Might one use Outlook 2013 and, rather than "connecting" to Outlook.com, simply set up an IMAP account for Outlook.com.  Which is better / less likely to need support?

I think Outlook 2013 is best. It is what I use and have no issues with it. Either way you connect it should work.
0
Fred MarshallPrincipalAuthor Commented:
John:  What's your definition of "push" in a case like this?
0
JohnBusiness Consultant (Owner)Commented:
The person at home here gets a couple of emails a day. I get about 25 per day, have mail going back to 1996, use Calendar, Tasks, Notes, sync it all with my iPhone and generally pound on Outlook all day long.
0
Fred MarshallPrincipalAuthor Commented:
John:  OK.

I'm also wondering about outlook.com / Hotmail as an email service provider.
That's because the user has an ISP that provides email service.

If we switch from Hotmail to the ISP then the email address will change which will be a big deal.
Yet, I wonder if  that server isn't also something flaky?

One thought is to install Thunderbird with an IMAP account and see if the behavior is any different vs. Windows Live Mail at the same time / time frame.
0
JohnBusiness Consultant (Owner)Commented:
Outlook has a connector to download email from Outlook.com. It may just be an available add-in since Microsoft owns both.

Thunderbird can do this as well and Thunderbird is better than Windows Live Mail also.
0
Fred MarshallPrincipalAuthor Commented:
John: Thanks for the advice!
Is the person at home using POP or IMAP?

As I said, I wanted to preserve the use of Windows Live Mail 2012 on Windows 8.1 if possible.
But we certainly did consider buying or leasing Outlook 2013 as an industrial-strength solution.

IMAP simply did not work well between Windows Live Mail 2012 and Outlook.com.  It was very slow and there were any number of server disconnects happening to the point that it was nearly unusable.

Switching to POP3 seems to have solved the problem.
It was pretty tough finding the CURRENT settings for it.  Here they are:
Incoming server: pop-mail.outlook.com / Port 995 / SSL
Outgoing server: smtp-mail.outlook.com / Port 587 / SSL

Getting Windows Live Mail to use Port 587 with SSL was a bit tricky.  Often, after checking SSL, it would switch the port number back to 25.  But both 587 and SSL are needed for it to work.
To be honest, I don't recall which sequence of entries I used to get it to stick - but it did stick in the end.
I think maybe it was: enter 587, check the box for SSL and then hit Apply immediately (and not Enter).
Somewhere I read that if TLS isn't available as a setting (it isn't with Windows Live Mail) then use SSL.  That does seem to be the case.
Other places say that Windows Live Mail doesn't have the required TLS so it won't work.... obviously not correct.
0

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
JohnBusiness Consultant (Owner)Commented:
I use POP3 with Outlook 2013 (Office 2013 on subscription) and Outlook is fine with the needed ports (995 / 587 or 465 TLS).  The other person here uses Windows Live Mail on Windows 7 via POP3 (not IMAP) and it works fine for low volume.

We use Live Mail on Windows 7 because I use Outlook 2010 on the same machine with the same userid.

I am going to change the Windows 7 machine for Windows 10 as soon as I can, and I will likely use Thunderbird on the Windows 10 machine because I will put Office 2013 on the Windows 10 machine.

I hope this helps.
0
JohnBusiness Consultant (Owner)Commented:
Incoming server: pop-mail.outlook.com / Port 995 / SSL
 Outgoing server: smtp-mail.outlook.com / Port 587 / SSL
Getting Windows Live Mail to use Port 587 with SSL was a bit tricky


I use Port 465 / TLS on my Outlook setup. The Live Mail setup uses 587 and sometimes we have problem sending mail (intermittent).
0
Fred MarshallPrincipalAuthor Commented:
John:  It looks like you just quoted what I said works.  
But are you using POP or IMAP with Windows Live Mail accounts for outlook.com?  It seems to make a huge difference.
0
JohnBusiness Consultant (Owner)Commented:
I am using POP3 for both applications. I like email on my computer more than on the web.
0
Fred MarshallPrincipalAuthor Commented:
I agree with having the email on the computer for a number of reasons:
- when working on email it's generally a lot faster.
  .. faster to open
  .. faster to view emails
  .. etc.
- the ability to use other app's to send emails is there.
- there is generally an editor that's of your own choice.

The only reason we used IMAP at the beginning was to avoid confusing the neophyte user - who was hard pressed to know the difference between Outlook.com web mail and Windows Live Mail pointing to the same account at Outlook.com.  It turned out to be an exercise in futility as IMAP didn't work well at all.
0
Fred MarshallPrincipalAuthor Commented:
Juggling email servers with email clients and protocols is often a challenge.
This started out being about IMAP which wasn't really discussed.
A solution for POP / Outlook.com mail was provided that's up-to-date.
0
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Windows 8

From novice to tech pro — start learning today.