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Hotmail email issue keeps happening

No matter what I do, I always end up having to restart my macbook pro to get into my Hotmail account through the Apple Mail app. It'll work properly for a few days, but then after that it keeps prompting me to enter my password, which I know is correct, I'm copying and pasting it directly into the password field and I can type it into the password field too, nothing works. So I end up having to restart my computer completely to be able to access my Hotmail account, which isn't too big of a deal, but it'd be nice if I didn't have to do that. Picture of issue provided. I searched for a way to post this in the Mac OSX Mail App area, but couldn't find it, if this is the wrong place for this post, please point me to the right one, thanks!


MacBook Pro 15", macOS 10.15

Posted on Apr 8, 2020 9:58 AM

Reply
Question marked as Top-ranking reply

Posted on Apr 8, 2020 12:35 PM

Open Keychain Access in Utilities, use Keychain First Aid under the Keychain Menu item, then either check the Password under that item, change it, or delete it and start over.


You may have multiple entries.


Open Keychain Access in Utilities, enter the part after the @ sign in the search bar, hit enter


You may have multiple entries. You can edit them or delete them & start over.


Mail will most often use the oldest passwords.

14 replies
Question marked as Top-ranking reply

Apr 8, 2020 12:35 PM in response to G. Thorson

Open Keychain Access in Utilities, use Keychain First Aid under the Keychain Menu item, then either check the Password under that item, change it, or delete it and start over.


You may have multiple entries.


Open Keychain Access in Utilities, enter the part after the @ sign in the search bar, hit enter


You may have multiple entries. You can edit them or delete them & start over.


Mail will most often use the oldest passwords.

May 6, 2020 7:21 AM in response to BDAqua

BDAqua, I thought I posted a comment yesterday, I guess I didn't hit send. I'm having trouble narrowing down the passwords for Mac Mail. I just noticed something in your comment above, you said Mac Mail almost always chooses the old Passwords if you don't change or get rid of the old ones. What exactly do you mean by that. It's prompting me to type in my password every time I login, and I'm typing it in correctly, I know I am, this isn't something that is automatically there. As I started saying in my comment here, I'm having trouble locating which keychain is connected to the mac mail app. There are so many keychain "items" or "files" (screenshot provided) and the way they're listed is very confusing. I went a step further and typed in @hotmail in the filtering search field to try and narrow down the search, but it's still hard to find which one is connected to mac mail. I blurred some things out in the screenshot I'm going to post, but I'd be more than happy to remove the blur and show you all of the contents if you'd like to see them. The two items I left without the blur are just for context, I don't believe they're attached to my hotmail account in any way. Thanks again!

May 4, 2020 4:51 PM in response to G. Thorson

I'm removing the First Aid reference as it no longer applies, so both I'd think.


In a Browser can you login?


How to access my e-mails using http://hotmail.com?


Step One: From any computer that has Internet access, start a Browser.

Step Two: Go to http://www.hotmail.com.

Step Three: When you are prompted for a user name and password, enter the following information:

E-mail Address: Enter your MSN member ID and @msn.com in this format: msnmemberid@msn.com.
Password: Enter your MSN member password.

Step Four: Click Sign-In.

Last Step: You will be signed in to Hotmail with your MSN account. Click the Mail tab at the top of the screen to display your MSN inbox.


May 4, 2020 5:42 PM in response to BDAqua

Thanks for the quick reply. Yea in the Browser, I have bo problems at all, it's just with my hotmail account and the Apple Mail app. The mail app is one of the best I've used, it's so streamlined and simple yet has all the features I need. I'm wondering if changing my password for my hotmail account would make any difference. I'm a bit hesitant on doing that though, because I'd have to re-enter it in a bunch of different places, which is only a minor annoyance, but still. :)

May 4, 2020 5:52 PM in response to G. Thorson

I wouldn't change the password, Mail makes it difficult to change the PW if one of Mail\s Auto setup accounts, but...


Open Keychain Access in Utilities, then either check the Password under that item, change it, or delete it and start over.


Enter the part after the @sign in the search bar.


You may have duplicate or more entries in Keychain Access.


If using a browser to login via WebMail works it's not Name or Password, but likely old passwords interfering.


There''ll be at least 2 entries, maybe more.


The trouble is that Mac Mail almost always chooses the old Passwords if you don't change or get rid of the old ones.

May 6, 2020 10:50 AM in response to G. Thorson

What exactly do you mean by that. It's prompting me to type in my password every time I login, and I'm typing it in correctly, I know I am, this isn't something that is automatically there.


Exactly, you type in the new correct PW, Mail looks up the old one in Keychain & sends that if there is one, doesn't matter what you type. Mail in iOS seems to handle it correctly or replaces the old PW, but not MacOS.


Those may not be for Hotmail...is your eMail @hotmail, or @outlook, or what?

May 20, 2020 9:30 PM in response to BDAqua

Sorry for taking so long to get back to you at times. I don't use forums that often and when I do, as you can tell, I get a bit forgetful. The deal is I haven't CHANGED my password for a very long time, that might have been lost in translation thru our conversations, I wish I could go back and see when I updated to this newER password, it might have even been before I got my MacBook Pro, meaning I wouldn't have had this issue for a long time 'til after I got my MacBook Pro. Also what was the need for the mention of iOS, I only own a MacBook Pro and a very old obsolete iPad 2 that I rarely get on, although it does have my email accounts attached to it. All of my other devices are Samsung Galaxy, including Tablets, this is only happening in the MacOS mail app and only for that one hotmail.com account and it is @hotmail.com for the suffix on the email account. Thanks for sticking with me through all of this.

Hotmail email issue keeps happening

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