Mail will not send after upgrading to Mavericks

I have a fairly similar problem. Upgraded to Mavericks recently, and have just changed ISP too. Internet access all working properly, but today tried to set up new POP email with new ISP.

All settings are correct, but when I try to access the new mailbox in Apple Mail 7.0, I am asked to give my password. I enter it, and all I get is the same request again, about ten seconds later - every time.

I notice that when you set up a new e-mail account, there is no option offered to have no SMTP authentication. There used to be in earlier versions of Mail under earlier OS versions. There was a check box you could leave unchecked when you wanted no authentication.

My ISP help desk says they don't require authentication for their e-mail accounts, and are puzzled that the Apple Mail set up now forces at least password authentication.

I have noticed, however, that editing the SMTP server list in Mail Accounts preferences does offer an option for no authentication. My ISP is currently resetting my accounts at their end, so it will be tomorrow before I can test whether that, or anything else has changed, but there is clearly an SMTP server problem in Mail, as is clear from the reading of posts about problems like this I've been doing in the last few hours.

Tom

I had the same problem, after three long days finally I resolved it. Some ISP block port 25 for outgoing mail SMTP I just changed to custom to 2525.

In mail preferences highlight the account with the problem, next to SMTP and your email address clik for the cascade window, click on edit SMTP server list uncheck use default ports, check use custom and enter 2525 then ok. Try to send an email and see what happens you can always go back and set the original setting.

Hope this will help

mpubco,

My ISP's helpdesk has solved my problem for me this morning. However, I don't think the solution is going to help you.

Turns out that the previous Support Desk guy I spoke to (yesterday) gave me wrong advice about the format for my user name in the Apple Mail settings. That was picked up today and corrected, and, at the moment at least, I have mail working just fine under Mail 7 and Mavericks on a brand new account.

I hope you get your issues solved soon.

Tom

same problem, icloud and exchange too, and I can't edit the server for iCloud. now no mail is sending

I have to keep deleting the smtp server for optonline and adding it back to send out mail using mavericks. Why?It only lasts for a couple of weeks and i have to do it again. Any permanent fix?

Same problem with my ICloud email account -- I think I have entered the "smtp" info 12,000,000 times. It's as if I think if I think if I keep doing it over and over I am going to get a different result. Having grown up in a town with a state mental hospital -- I am geting really worried about myself because isn't this process I am using the definition of insanity H-E-L-P!!!!!!!

Also, the incoming mail server box for my ICloud account has a shaded address in it that I cannot delete "p05.imap.mail.me.com" and before changing to Maverick my email address was my old "aol" address for ICloud and now it is shaded in as an "icloud.com" address. My old aol address is not even listed as a alias??????

I'll be watching for an answer -- thanks.

If you're getting endless prompts to enter your password in Mail, try this. First close Mail.

1. Open Keychain Access. This can be done through the spotlight or Applications > Utilities > Keychain Access.

2. Select the Login keychain on the left side.

3. In the search at the top right of Keychain Access, search the term "smtp" (without quotes).

4. You should see something like this come up in the list. For this demonstration I am using my live account.

You see the incoming and outgoing server entries, in many cases you may have multiple entries.

5. Ensure you have the correct password by logging into your webmail access for your email.

6. Delete the entries for the server that is giving you issues by Control + Click the file and Delete "smtp.server.com" or "pop.server.com".

7. Close keychain access and restart your computer.

8. When you open Mail again, it will prompt your for your password.

9. Re-enter your password and it will create a new keychain entry.

This should resolve the issue. Keep me updated.