Suddenly iMail won't play nice with my Hotmail accounts. Help?

Yesterday I received a Security Alert from Microsoft that someone may have accessed my two hotmail accounts. I have had one for 20 years and another I've had for 10 years for professional/job-seeking use, and I can't just walk away from them unfortunately, even though Hotmail has never really played "nice" with iMail, occasionally falling into that loop where iMail keeps asking for passwords, etc.

For both accounts I went thru Microsoft's routines of changing my password as well as adding Google Authentication to both. For one I even added an "app password," which was new to me -- for that one I use a special/different password for my iPhone just for that account. For some reason that option exists for only 1 of the hotmail accounts.

At any rate, iMail needed new passwords obviously but wouldn't take any of the new ones. I deleted both hotmail accounts from iMail and re-introduced them. iMail seems to receive mail from them no but won't send any. Outgoing messages just sit in the Outbox.

I have Lion version 10.7.5 and version 5.3 (1283) of mail, a few generations old since I'm limited with my 2006 mac.

Anyone recognize this and have any advice? Thanks a lot.

Mac Pro, Mac OS X (10.7.5)

Posted on May 17, 2014 4:20 AM

31 replies

May 17, 2014 6:07 AM in response to Csound1

Csound1 - I hear you, believe me, what a pain. But I'm posting here since my main issue is that Mail @my mac pro won't send mail. I have everything else working happy - iphone, ipad, etc. In fact I can receive mail at my mac pro Mail app, just can't send. painful!!

Csound1

Level 9

60,063 points

May 17, 2014 6:08 AM in response to Pittsburgh Andy

This is a question for the vendors whose services those are, not Apple.

LD150

Level 10

101,796 points

May 17, 2014 6:09 AM in response to Csound1

Agreed. I would never use two step authentication whilst trying to use email clients anyway.

May 17, 2014 6:18 AM in response to Csound1

Frustrating. Having gone in and out of my accounts the past 2 days, it seems that the authenticator app is just for when trying to get to the Security Settings for either hotmail account, or when trying to change the password from the homepage of www.hotmail.com w/o having logged in first. So I'm pretty sure the authenticator has nothing to do with my apple mail problem. I just mentioned the fact that I added all kinds of new security options to my hotmail accounts yesterday thinking that maybe one is causing my can't-send-mail problem. I'm pretty sure they don't matter, since I can receive mail with my mac pro mail program....just can't send....even after re-setting up the accounts. Seems like it'd be an Apple problem but who knows. So very very frustrating, right on top of my (red herring alert) frustration with ios7's horrible interface and design and frustration with the entire online community follwing like lemmings into this boring flat design cliche that makes things more vague and harder to navigate rather than easier! 🙂

Anyone who can help me fix my can't-send issue will be sent a $10 starbucks gift card - first one to solve the issue gets it, ha ha. Please help me if you can. 🙂 Thanks!

May 17, 2014 6:19 AM in response to LD150

Peter - I think the two-step is great in this sense - it's much easier for me to wade into my account using a separate authenticator app if there's an issue with my password. Now, having to go thru 2 steps when accessing email from a new computer - yes, that may be causing the problems, who knows. So strange that I can receive but not send. Argh.

Csound1

Level 9

60,063 points

May 17, 2014 6:52 AM in response to Pittsburgh Andy

Set it up without the authenticator app, if you are right it still won't work. But I suspect it will.

I found this (largely confusing) guide on how to use it, see if it helps.

LD150

Level 10

101,796 points

May 17, 2014 7:36 AM in response to Pittsburgh Andy

i would rather not try to use it, but if you do, from what I have been reading about it, you need to generate a single use application specific password for Mail in hotmail.com (outlook.com) then set up the account as new in Mac using that throwaway password.

LD150

Level 10

101,796 points

May 17, 2014 8:41 AM in response to LD150

I have tried it on a new account. I can't find any way of getting Mail (or Airmail) to acceot the wierd passwords. Can receive but cannot send, same as you.

The options for devices are...

Then Mail crashed.

Turn off two step verification is now my advice same as Csound1's was.

May 17, 2014 9:12 AM in response to LD150

Peter - bad news is that I have had two step verification shut off for the past day.

I removed every account from my Mail app on the mac and will try re-loading them.

I can't find another good mail program to use that will let me access icloud, hotmail, and gmail in one program....

LD150

Level 10

101,796 points

May 17, 2014 9:58 AM in response to Pittsburgh Andy

I use Airmail from the App Store. Couple of bucks.

May 17, 2014 12:56 PM in response to LD150

Peter I'm loving airmail. A million times better than the standard Mail app. If I have no password or other problems with airmail, you win the starbucks, assuming you're a starbucks fan?

Thanks a ton - so far so good.

Asking for a replacement for Apple's standard mail app was the real question I should have asked.

LD150

Level 10

101,796 points

May 17, 2014 1:15 PM in response to Pittsburgh Andy

In the UK that brand will only be popular when they change their corporation tax practices, but I will have a Costa coffee instead. Airmail has improved a lot in the last six months and IMAP webside folders makes it easy to change. Airmail not so easy with local folders.

May 17, 2014 1:18 PM in response to LD150

Do you mean local folders as in - on the computer itself? The most important thing to me will be to be able to access the folders in icloud both in airmail and away from home on the ipad & iphone. What limitations do you speak of specifically?

I'll look for Costa coffee online then...

LD150

Level 10

101,796 points

May 17, 2014 1:19 PM in response to LD150

By the way Airmail will add three folders (to do, reminders etc) to all your accounts webside. Even in iCloud account.

You can turn that off in the settings of each account and delete them from there if it annoys you, but they do no harm.

LD150

Level 10

101,796 points

May 17, 2014 1:25 PM in response to Pittsburgh Andy

Some people archive all their to-keep mails on the Mac, whereas some keep them as folders in the online account, which I do, so they can as you say be accessed from anywhere on any device. Some people don't want MS or Google to keep their old mails and use local folders in Mail which Airmail is not strong on, in fact previous versions had a big bug on that.

Overall Ii think Airmail has fewer bugs and is faster managing IMAP syncing.

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Suddenly iMail won't play nice with my Hotmail accounts. Help?