Recurrent Mail error: "The server rejected the password"

I've gotten this error message in various versions of Mac OS X on different Macs.
Occasionally this dialog will pop up in Mail saying:
Enter Password for account _______
The server rejected the password for user [my email].
Enter your password again or cancel
Then at the bottom of the dialog there's a checkbox to "Remember this password in my keychain"
Even though I ALWAYS check that box when entering my password, when that error comes up, the box is always unchecked!!
Does the fact that the box is unchecked mean that Mail thinks the password is NOT stored, and if I fail to enter my password again, it will simply stop trying to access my mail?
Is there a way to tell Mail that, since I have stored the password already in the keychain, just keep trying and don't give me that annoying message?

Pages 5.5.2
As I understand it a .5xx pages file (.pages) is actually a folder and is therefore compressed into a zip file when emailing. Certainly, when you email a .pages file (recent version), it arrives as a .Zip even though you don't compress it. I'm pretty sure this was NOT the case with earlier versions.
The key thing here however, is not so much sending a .pages file or any other.zip file - these can be sent by iCloud quite happily. It is about why iCloud won't receive them. If I send a .pages or .zip file from iCloud to my business email, it arrives without any problem. If I send to my iCloud address I get the message size violation - every time.
And just to re-iterate, I have tried sending Zips and Pages files to several other iCloud accounts and they ALL had the same issue.

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The server rejected the sender's email address.

The message could not be sent because the server rejected the sender's email address. The sender's email address was '[email protected]'.
Subject 'Fw: trade brochure'
Server Error: 530
Server Response: 530 authentication required - Your email could not be sent. To fix this you must make a simple change to your email client (known as SMTP authentication). For advice visit http://www.bt.com/smtp
Server: 'smtp.btinternet.com'
Windows Live Mail Error ID: 0x800CCC78
Protocol: SMTP
Port: 25
Secure(SSL): No
this message keeps appearing every time i try to send an email from my account, please could you help me x

Hi,
You need to
check the box next to "My outgoing server (SMTP) requires authentication"
on the Outgoing Server tab and select the radio button for "Use same settings as my incoming mail server."
Since I don’t know which version of Outlook you are using, the third-party link below may be helpful to you:
Setting up Business Mail in Microsoft Outlook 2010 and 2013
In addition, you can ask in the forum below for further assistance:
http://answers.microsoft.com/en-us/office/forum/office_2013_release-outlook?sort=lastreplydate&dir=desc&tab=Threads&status=&mod=&modAge=&advFil=&postedAfter=&postedBefore=&threadType=All&tm=1386067216493
Best regards,
Susie

On the iPhone, when the server rejects the email address and it sits in the outbox, why doesn't it automatically resend when the server is fixed?

On the iPhone, when the server rejects the email address and it sits in the outbox, why doesn't it automatically resend when the server is fixed?

Hi Razmee,
Thanks for your response.
The mail server worked when I originally set it up and continued to work for months afterwards.
What would make the outgoing mail server not be set up correctly after all that time?
Thanks again.

I just updated my IPad to iOS 5 and now can not send email. The error message says the server rejects the address which is not true Asti sends on my desktop.

I just updated my iPad to iOS 5 and now can't send email- I have tried the obvious but no luck. Any suggestions?

Usually 'authentication required' means that you need to submit a username (or e-mail address) and password to the e-mail server, when sending a message. This logic is not different between Outlook and Thunderbird, and even with the latest and previous version of Thunderbird.
Of course you can try the previous version again to see if it solves the problem, although you'll be less secure because you would be missing the latest fixes.
If you'd be willing to get back to Thunderbird, say if your frustration level with your new app would increase too much, please see our article [https://support.mozilla.org/en-US/kb/cannot-send-messages cannot send messages] for further help.
In all other cases I'd appreciate it if you could mark this as answer so we know you don't need further help.

Intermittent "The mail server rejected the password" on SBC-Yahoo

I have Mail set to automatically check email every 5 minutes from an SBC-Yahoo DSL line.
*Every day* when I come home, the "Server rejected the password" error dialog is waiting for me. Of course, the password is correct. When I re-enter it, Mail downloads the mail correctly.
This problem seems to occur more often since I switched over from the old prodigy.net to the sbc.yahoo.com servers.
While I sure wished that Mail was not totally boneheaded in handling the occasional failed POP connection attempt, I wonder whether:
1. I am the only one having this problem
2. It's a Yahoo problem
3. Is there a way to fix it?
TIA

I have Mail set to automatically check email every 5
minutes from an SBC-Yahoo DSL line.
*Every day* when I come home, the "Server rejected
the password" error dialog is waiting for me. Of
course, the password is correct. When I re-enter it,
Mail downloads the mail correctly.
This problem seems to occur more often since I
switched over from the old prodigy.net to the
sbc.yahoo.com servers.
While I sure wished that Mail was not totally
boneheaded in handling the occasional failed POP
connection attempt, I wonder whether:
1. I am the only one having this problem
2. It's a Yahoo problem
3. Is there a way to fix it?
TIA
I am having the same problem. I have to re-type my password for two POP accounts each time I start MAIL. It doesn't hold the SMTP passwords either.
Once I go into the preferences and re-type them it will connect fine until I restart MAIL and I have to start all over again...I too wonder the same things!

The iCloud server rejects my password

As of the past 36 hours, whenever I try to get (download) my mail ("Mail" via iCloud) a pop up window appears that states...
The iCloud IMAP server “p02-imap.mail.me.com” rejected the password for user “me”
Enter your password again or cancel.
I enter the valid password (which was functioning just a few days prior), yet once again the server rejects my password. Hence, I haven't been able to retreive my mail now for going on two days.
I have not changed my password or any other data (related to iCloud or the "Mail" program in a about a year. If I recall correctly I had updated the Safari program and I think a Java or Security item the previous day.....
Can anybody (please) supply me with some information or tips on how I can retreive my mail and get this #%& program functioning properly again?

Thanks Csound1... that worked and then on a hunch I immediately opened my 'Mail' program clicked on get mail and entered the same AppleID and password and this time.... for some incredible bizarre reason, my mail program worked and displayed all of the last few days mail.
Thanks again.

OS Lion Mail: Microsoft Exchange Server Rejects Password

Hello,
I just upgraded to Lion and was attempting to set up all of my email accounts into Mail. My Yahoo, AOL, and Gmail accounts all worked fine, but my Microsoft Exchange account did not. When I set it up through Settings originally, everything seemed fine and it had no problem verifying the account. However, when I try to retrieve mail from the Exchange account within Mail, it gives me an error saying that the server rejected the password and then prompts me to enter the password again. I enter the correct password, and the same window pops up over and over again. Has anyone found a fix to this problem?
Thank you!

Same Problem here since days and nobody at Apple is picking it up, even though a lot of people experiencing the same issues.
I Tried deleting all accounts (GMX, Exchange) from Mail 5.0 and create a new one (only Exchange) here: "System Pref". -> "Mail, Contacs & Calendars". Account creation worked, but Mail keeps asking me for the password telling me the server rejected the pw, which is correct (as it worked with the account creation).
To be honest I'm a little disappointed, having switched from PC to Mac earlier this year and never ran into problems with a PC that took me longer than a day to fix (especially on productive systems!), i start to regret buying a mac...
Cheers

Server rejected the address

What does it mean when you try to send an outgoing message and you get the "server rejected the address ____" message?? It's odd b/c I tried sending mail to two people, and when I took that other one off the message it went through. This is someone I email regularly, too, so not sure why it would be doing that.
thanks

Was this in the To:, CC:, or BCC: field ?
Have you tried just sending to that one failed one alone?

Can't send mail, get message: the smtp server rejected the password. I tried lock and unlock keychain. I tried unlock captcha. Gmail works okay, it is Mail that does not. Help!! :(

Can't send mail, get message: the smtp server rejected the password. I tried lock and unlock keychain. I tried unlock captcha. Gmail works okay, it is Mail that does not. Help!!

Hi
You need to check with your ISP whether or not the send mail server (SMTP) requires a password. Some do, but many do not. When you know the correct password to send mail, then you need to tell Mail as follows:
Mail menu > Preferences > Accounts > Select the account
Click on the Outgoing Mail Server (SMTP) combo box, and select Edit SMTP Server List...
In the Account Information tab put the server name
In the Advanced Tab, set up the authentication information from your ISP.
Good luck
Bob

Mail: The POP server rejected the password for user

I am completely unable to use Mail.
I keep getting the "The POP server rejected the password for user" on two of my accounts.
The password has not changed and I have entered it correctly.
The accounts just will not go online.
This started yesterday when an old machine accidentally fired up mail and tried to connect using the same user details. Since then, my MacBook Pro is not able to connect to my mail.
My iPad and my iPhone can. There is no problem at the server or the ISP. I have also run the Keychain repair utility.
Please can you advise how I should fix it? Plist? Define the accounts again?
Any ideas welcome.
Thanks

Sorry I can't be of help, I know of others with this problem. In my case I have two accounts that don't work in Mail whilst the other accounts do. I suspect it may be a bug as I've been looking for a solution for sometime. My current solution is to collect the mail on those accounts with an XP netbook which is probably not very helpful!
I have also tried the Keychain repair and at least for a short while it looked as if it had fixed it.
Any ideas anybody before I go through the hassle of reinstalling everything?
D

Can not receive Mac mail -error Outlook cannot find the server. Verify the server information is entered correctly in the Account Settings, and that your DNS settings in the Network pane of System Preferences are correct. Account name: "MacMail"

Can not receive Mac mail -error Outlook cannot find the server. Verify the server information is entered correctly in the Account Settings, and that your DNS settings in the Network pane of System Preferences are correct. Account name: "MacMail"
What are the correct mail account settings and more importantly the correct DNS settings
Thank you for any help you may be able to provide
Cheers
Chris (iMac i7)

Do not delete the old account yet. sign up for an iCloud account if you haven't.
I understand .mac mail will still come through. Do not delete the old account yet.
You cannot use .mac or MobileMe as type of Account, you have to choose IMAP when setting up, otherwise Mail is hard coded to change imap.mail.me.com to mail.me.com & smtp.mail.me.com to smtp.me.com, no matter what you try to enter.
iCloud Mail setup, do not choose .mac or MobileMe as type, but choose IMAP...
On second step where it asks "Description", it has to be a unique name, but you can still use your email address.
IMAP (Incoming Mail Server) information:
          •          Server name: imap.mail.me.com
          •          SSL Required: Yes
          •          Port: 993
          •          Username: [email protected] (use your @me.com address from your iCloud account)
          •          Password: Your iCloud password
SMTP (outgoing mail server) information:
          •          Server name: smtp.mail.me.com
          •          SSL Required: Yes
          •          Port: 587
          •          SMTP Authentication Required: Yes
          •          Username: [email protected] (use your @me.com address from your iCloud account)
          •          Password: Your iCloud password
Also, you must upgrade your password to meet the new criteria: 8 characters, including upper and lower case and numbers. If you have an older password that does not meet these criteria, when you try to setup mail on your mac, using all of the IMAP criteria listed above, it will still give a server error message. Go to   http://appleid.apple.com         then follow directions to change your password, then go back to setting up your mail using the IMAP instructions above.
Thanks to dpepper...
https://discussions.apple.com/thread/3867171?tstart=0

HT4864 I am getting a triangle with an exclamation point next to my inbox...it says: There may be a problem with the mail server or network. Verify the settings for account "MobileMe" or try again. The server returned the error: Mail was unable to log in

I can send but cannot recieve email
This is the messege I am gewtting:
There may be a problem with the mail server or network. Verify the settings for account “MobileMe” or try again.
The server returned the error: Mail was unable to log in to the IMAP server “p02-imap.mail.me.com” using “Password” authentication. Verify that your account settings are correct.
The server returned the error: Service temporarily unavailable

Also if I go to system preferences accounts and re-enter the password it fixes the glitch sometimes.

POP server reject the password for....

Dear All,
I am trying to set-up the mail client of my macmini runing Lion Server (on the same machine), but I get the message
"POP server reject the password for user "John".
As I am not an expert on Lion Server, can anyone please tell me what I am doing wrong.
The loggin account name on the server is "John", PW is "1", domain is "exemple.jp"
The mail address is concequently [email protected]
1st: is the POP server PW different from user loggin password?
2nd :is there a place on the mail pop server for user password.
3rd: how does this work??
Thanks for any help.
Bruno

Sorry I can't be of help, I know of others with this problem. In my case I have two accounts that don't work in Mail whilst the other accounts do. I suspect it may be a bug as I've been looking for a solution for sometime. My current solution is to collect the mail on those accounts with an XP netbook which is probably not very helpful!
I have also tried the Keychain repair and at least for a short while it looked as if it had fixed it.
Any ideas anybody before I go through the hassle of reinstalling everything?
D

Cannot Send Mail, the server rejected one of the recipient's addresses.

I receive mail just fine. Can't send anything

Interesting to read all your posts, as I too have had this issue with my BRAND NEW Wi Fi 3G 64 GB ipad. Everything worked perfectly well with wireless at home, then we left for a trip interstate. First night I tried to send three emails and received the message that the server had rejected one of the recipients and the messages had been placed into the out box. Most annoying, as the out box is not accessible. I phoned apple and, after much discussion, it was suggested I call my ISP (BigPond). Another lengthy discussion and it was noted that there were no messages in my out box on the server, therefore the issue was with the ipad. I downloaded gmail and was able to receive and send emails using that program. Was also able to access my emails via Big Pond's web mail. It was just the mail program on the ipad that continuously looped back to the same error message. I deleted the account and decided to ask for a refund on the ipad. Back home, I have reinstalled mail to my Big Pond account and all seems to be working well. Am not sure what to do next, as I will be very disappointed if this keeps happening. The ipad is an expensive investment and I want to be able to use it to its fullest extent. Otherwise, I love apple products and am a apple user of more than two decades.
Good luck all.

Cannot send email from my iPhone or iPad. The server rejects a recepient for no apparent reason. The recipient is not new. This issue happens on reply or reply to all or froward; not a new email. What is happening?

Cannot send email from my iPhone or iPad. The server rejects a recepient for no apparent reason. The recipient is not new. This issue happens on reply or reply to all or froward; not a new email to the same recepient. What is happening?

I talked with a tech today and he said I cloud is having problems which should be resolved shortly.
In the mean time I used the .me smtp server settings which allowed me to send mail.

Recurrent Mail error: "The server rejected the password"

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