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

Question

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

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Answer 1

Csound1

Level 9

60,063 points

May 17, 2014 4:34 AM in response to Pittsburgh Andy

Lets straighten things out a bit,

Google authentication has no function with a Hotmail account, what did you do?

Post the settings you are using for Hotmail access in Mail (not iMail) here, include the incoming and outgoing servers, ports and authentication method.

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Answer 2

LD150

Level 10

101,772 points

May 17, 2014 5:00 AM in response to Pittsburgh Andy

It also sounds like a phishing email. Did you click the link on the email to give all that Microsoft AND Gmail password information? or did you go to your hotmail in a browser and change the paswords there. I don't regongnise any of that app password and gmail authentication stuff.

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Answer 3

May 17, 2014 5:10 AM in response to Csound1

I agree with what you're saying about google authentication - what I was trying to convey is that I changed my passwords yesterday @hotmail as well as added a few things to each to increase security, such as adding google authentication to both accounts and adding an application pasword to the one account for which that option was offered. I also added 2-step verification that would require add'l authentication for login, to protect my accounts better, since something obviously weird happened the other night where two of my hotmail accounts were seemingly compromised within an hour, which I question but is another topic for another day! And I added a recovery code. I basically went all-in with increasing security on my accounts.

What I noticed was - when I tried to login to hotmail from a new computer, it required various additional checks from above to allow access to hotmail from that computer. Then when my iphone, ipad, and mac mail app needed new passwords, they all acted different and finicky - I'd be typing in the correct passwords that alllowed me to login to hotmail.com, and sometimes they would take, sometimes not. On the iPhone, I used the "app password" rather than my www.hotmail.com password for the one hotmail account, while I used the www.hotmail.com password for the other hotmail account.

Mail on my mac computer wouldn't take *any* password, even if I deleted all password entries for outlook from the Keychain Access, so I deleted 2 hotmail accounts in my mac computer Mail program and restarted - both receive mail and don't chronically ask for a password now, but neither will send mail. Here are my settings for both:

Account Information tab:

For the first hotmail account in my Mail app:

incoming mail server: imap-mail.outlook.com

outgoing mail server: Hotmal (first one available in pull-down menu)

Use only this server: checked

TLS certification: None

Advanced:

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Answer 4

Csound1

Level 9

60,063 points

May 17, 2014 5:16 AM in response to Pittsburgh Andy

Pittsburgh Andy wrote:

I agree with what you're saying about google authentication - what I was trying to convey is that I changed my passwords yesterday @hotmail as well as added a few things to each to increase security, such as adding google authentication to both accounts

For the last time, you can not add Google authentication to a Hotmail account, this statement is meaningless.

I asked for the details of the SMTP server, you have not provided it (Hotmail is not the name of a server)

Click on the box that says Hotmail and select Edit SMTP Server list and post screenshots of both tabs (select the Hotmail account)

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Answer 5

May 17, 2014 5:22 AM in response to LD150

Hi, Actually I received two text messages from hotmail alerting me that something was up.

I went to www.hotmail.com, tried to login, and couldn't get into either account - it diverted me to answering some security questions then let me in.

As for the google authentication, here's what my security options look like at hotmail.com (outlook) for the two acounts. Strangely, suddenly I don't see the option for the "application password" that I used for my iPhone mail for the one account. The google authentictor app is from the "Identity Verification Apps". It seems to work well - If I try logging into hotmail.com from a "new" computer, it asks for a randomly generated 6 digit code from my iphone google app.

Protect your account

Password

Your password was changed on 5/16/2014.

Change your password

Security info helps keep your account secure

When you need to prove you're you or a change is made to your account, we'll use your security info to contact you.

xxxxxx@icloud.com

Will receive alerts

(xxx) xxx-xxxx

Won't receive alerts

xxxxxxxx

Won't receive alerts

Add a new email address

Add a new phone number

Change alert options

Two-step verification

Two-step verification is an advanced security feature that makes it harder for a hacker to sign in to your account with just a stolen password. Learn more about whether this is right for you.

Set up two-step verification

Identity verification apps

You've set up an authenticator app. Learn more about identity verification apps.

Set up

Turn off existing apps

Recovery code

You can use your recovery code if you lose access to your security info. You need to print out your recovery code and keep it in a safe place.

Replace

Trusted devices

On your trusted devices, you don't have to enter a security code to access sensitive info (such as your credit card details). Learn more about trusted devices.

Remove all the trusted devices associated with my account

Close your account

Closing your Microsoft account deletes all the data associated with it.

Close my account

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Answer 6

Csound1

Level 9

60,063 points

May 17, 2014 5:25 AM in response to Pittsburgh Andy

OK, I give up

Good luck.

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Answer 7

May 17, 2014 5:28 AM in response to Csound1

Hi - Yes you can use google authentication for hotmail. See my above post. THis was new to me also. Under the "Identity Verification Apps" at www.hotmail.com within "Security & password" settings is the option to link your account with a Google authenticator app. Maybe that's new to you as it was to me yesterday?

Screenshot:

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Answer 8

May 17, 2014 5:29 AM in response to Csound1

Don't give up - that response that you responded to was intended for the person asking about phishing.

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Answer 9

LD150

Level 10

101,772 points

May 17, 2014 5:34 AM in response to Pittsburgh Andy

I stil, think you were phished. Change them all again in hotmail.com, delete the accounts from Mail and add them back with the new passwords. It is so unlikely Microsoft would have alerted you to two accounts simultaneously.

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Answer 10

May 17, 2014 5:37 AM in response to LD150

Hi - I did do that by going into www.hotmail.com directly at the time. You still think I should change the pw's?

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Answer 11

LD150

Level 10

101,772 points

May 17, 2014 5:50 AM in response to Pittsburgh Andy

"Yesterday I received a Security Alert from Microsoft that someone may have accessed my two hotmail accounts." just sounds wrong, like the ones from "my bank"

.

OK you did the right thing by going to hotmail in a browser. If the last access was genuinely to hotmail.com then probably no need to change again.

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Answer 12

May 17, 2014 5:54 AM in response to LD150

peter - thanks. I have no doubt that you guys helping me are smarter than I am with this stuff (and thus why I'm asking here) but does this sound legit or not to you:

The alerts arrived as texts to my iphone, from "837-401," and each time I changed my passwords yesterday (and just now, just to be safe), I received a confirmation text message from 837-401.

What a hassle this has been! 🙂 And the mail app on my mac pro still won't work. I was hoping Csound1 could help me but he seemed to have run out of patience??

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