Mac mail: Use SSL on SMTP Server turning on

I recently received and set up a new macbook pro (OSX 10.8.3) and I use it in both a wireless and wired network state.
I set up some POP accounts in my mac mail, and everything works great. But it seems that whenever I switch between networks, the "Use SSL" checkbox in my SMTP account for the mail magically turns on (I say "seems" because it could be some other factor such as actually changing to a completely different network location). At this point I can send out no new mails. I tracked this down fairly quickly, and annoying as it is, it *appears* at first glance to have a simple solution, go in and uncheck the box every time. However, the frustrating thing is, as soon as this occurs, I can't get the unchecked box to save. I'll go in, uncheck it, close it down, mail still won't send, and when I go back in I find it's still happily checked as "Use SSL".
The only way I've found to solve this problem so far is to delete the SMTP account, and then create a brand new one with the option unchecked. But having to do this every time I switch networks is ridiculous!
Does anyone have any thoughts as to what's going on or how I can *permanently* resolve this issue rather than resetting up my SMTP account over and over.

This seems to be a bug in 10.8.3. I submitted a bugreport and Apple replied this was a 'known bug'. Hope they fix it rather soon.

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Mac mail problem with gmail smtp server

I had 2 gmail addresses.
about 3 weeks ago mac mail decided to always send email from both addresses as if they originated from only one address.
I did not solve this problem.
For non related reasons, I got another gmail address.
The same thing started happening.
I now had 3 gmail addresses, but recipients were receiving all email from only one address.
I went to email preferences and started exploring and experimenting.
I was able to reconfigure so that the new gmail address sends from its proper smtp address.
However, there is nothing I can do to get my second email address to send from its proper smtp.
For some inexplicable reason the dialogue box beside "Outgoing Mail Serve (SMTP): tells me that smpt server is offline.
I have no idea how to get it back online.
(In the server editor, there is one more gmail smtp server than I need, 4 instead of 3 and 2 are offline - one just went off tonight)
All relevant mail boxes are online.
Does anyone know anything about this problem?

Jack,
There are mail forums in the forums for OS X, because you are using Leopard 10.5.6 (why haven't you upgraded to 10.5.8?) you should re-post in that forum. Mail comes as part of the OS that is why they're there. The address is:
http://discussions.apple.com/forum.jspa?forumID=1223
Regards,
Roger

Cannot send emails in Mac Mail using third party SMTP via BT Infinity Broadband

EUREKA!!
I have a Mac Book Pro and recently had my home broadband upgraded to BT Infinity. Prior to this upgrade sending emails via my Mac mail was working perfectly. Since the new installation I could no send any external emails using the Hotmail.co.uk or 123-Reg.co.uk smtp outgoing servers. Googlemail.com was ok.? very strange.
So when I connected the same macbook to other wireless connections it would work perfectly.???
So after many hours wasted messing around, I managed to get the right person at the right time via BT helpline in the UK not India. (India helpine just say "we are not trained in Apple".
So the very polite man from UK Helpline provided me with the solution.
GO TO > Apple Icon top left > System Preferences > Network > Wireless >
Select your wireless connection > Click Advanced lower right on popup
Select DNS tab
Click on the + under DNS left pane and type the following :- 208.67.222.222
Click Apply
BINGO!!!!
I hope this helps someone, as I know how painful these types of issues can be.
Cheers

Hi Haggie
Had a similar experience but couldn't work out why macbook was working and imac not. I hate verification with bt. Anyway, tried your method and as you say eureka! Did have imac plugged in before and put it on wifi to try your fix I will try plugging broadband back in to see if that works and will post back but at the moment just enjoying the moment!
Just to say a big thank you for not only sorting the problem out but equally importantly posting the answer! Too many people sort out their problems without letting other people know how!
Many thanks

Can port 25 be used for SSL-enable SMTP server ?

Hi,
Our customer is using port 25 for a SSL-enabled SMTP server without certificate. When our email client tried to connect to it, the following exception thrown:
DEBUG SMTP: exception reading response: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?
Since we don't want to ask our customer to change their port configuration unless absolutely necessary, we did some tests with our own SSL-enabled SMTP server that uses certificate. Here is what I got:
1) with port 25, got the same exception as above;
2) with port 465, worked fine;
3) with any other randomly pick up valid port, worked fine.
This made me wonder if 25 is for non SSL SMTP server ONLY. By the way, I'm using Javamail 1.3.4 and JSDK 1.4.2_02. My question is whether we can configure javamail so that port 25 can be used by SSL-enabled SMTP server?
Your help will be appreciated.

Yes, port 25 is intended for non-SSL servers only, although that doesn't
prevent a client from making a plain text connection and then using the
STARTTLS command to switch the connection to SSL/TLS. JavaMail 1.4
supports that usage.
You can configure JavaMail to use port 25 for SSL connections if you
really want to. JavaMail 1.3.x requires you configure an appropriate
socket factory to get SSL connections; you can configure whatever port
you want for use with that socket factory.

Configuring SquirrelMail to use SSL with SMTP

I ran the conf.pl script to have SquirrelMail access my IMAP server via SSL, and everything works.
I then tried to use SSL with SMTP as well but when I used SquirrelMail to send mail, I got an error saying "Can't open SMTP stream". What is the correct setting to tell conf.pl to use?
I had secure SMTP enabled and chose CRAM-MD5 for the authentication method.
I actually have my web server and smtp server on the same machine, so this is more of a hypothetical question. In the end I turned off secure SMTP and set authentication back to none.
Ben

I don't have access to logs right now, but to answer your other question, SSL works fine when sending from Mail.
But with Mail, I supply the username and password; which user does SquirrelMail use to send?

Cannot send email w/mac mail using Juno and Tiger

Hello!
I have had a problem ever since I upgraded last year to Tiger. I have Juno, and ever since I upgraded from Jaguar, I cannot use the Juno software to log on. But more annoying that that (I have a work around that works just fine), I cannot send email from my mac mail. If I want to send an email or respond to an email, I have to physically log onto Juno's website and email and write and send from there. I have contacted Juno numerous times, and they tell me to reset my password, which makes no sense to me. Any Ideas?

Regarding not being able to send mail with your .Mac account and .Mac SMTP server, most if not all ISPs used for connecting to the internet block the use of SMTP servers outside of their network on Port 25. Some ISPs allow the use of an authenticated SMTP server only (such as the .Mac SMTP server) that is outside of their network on Port 25 but some block its use regardless. These restrictions are in place as part of an overall effort to prevent or reduce spam eminating from the ISP's domain.
Something to try.
Go to Mail > Preferences > Accounts and under the Account Information tab for your .Mac account preferences at the SMTP server selection, select the Server Settings button below.
At the Server Port field, enter 587 in place of 25 and when finished, select OK to save the changed setting.
If this is not successful, select/use your ISP's SMTP server to send mail with your .Mac account which is invisible to all recipients.

Mac Mail Uses wrong "from:" Address .... ouch!

I have multiple e-mail accounts set up on Mac mail. Each email account has it's own SMTP server defined. The "use only this SMTP server" is checked on all the accounts.
Today I sent an email from one account ... let's call it [email protected]
The outbound server was set properly.
The mail was sent, and appears on the outbox for [email protected] Just like normal.
I got a reply back from the person I sent the e-mail to, and the reply shows that my e-mail originated from a DIFFERENT account. Let's call it [email protected]
The e-mail I sent originally does NOT show up in the Sent e-mail box for [email protected] It shows up in the Sent e-mail box for [email protected] where it should.
So ... it looks like Apple Mail sent an e-mail from the wrong account, using the wrong SMTP server. The mail program obviously doesn't konw what SMTP account to send mail from.
Wow.
I'm shocked.
This is beyond lame.
lame
lame
lame
lame
Has anyone else seen this?
--R

Follow up to my own question. I do see others have had this problem:
https://discussions.apple.com/thread/2253932?tstart=0
It makes no sense whatsoever for Apple Mail to "fall back" to an SMTP server that is not assigned to a particular account. It's far better for the SMTP connection to fail and NOT send the e-mail from the wrong account, instead of confusing all the people I send e-mails to.
This SMTP fallback "feature" ***** and should be gotten rid of.
it *****
it *****
it *****
it *****
--R

I have multiple accounts using the same smtp server, I can only reply with one as the settings wont allow me 2 servers

I have tried to set my email to reply from my iphone 5 both of which use the same SMTP server. I can't change the settings on the others as it will only allow one mail account. Can I add multiple with the same smtp?

I Am not using gmail I use seperate company for my mails both use the same smtp server. The problem is when I set my first account it them uses these details and passwords when I create the second account saying that the smtp server is already in use by the primary account. I therefor can't set the password.

Mail.app: Select outgoing (SMTP) server per message?

Dear community members,
I'm looking for a solution to the following problem:
I do have multiple e-mail accounts which are configured in the following way: One of them is the master account (let's say [email protected]) added to Mail.app as a POP account. The other ones (let's call them [email protected] and [email protected]) are on different servers and are configured to forward all incoming mail to [email protected] They are, however, not added to Mail.app as additional accounts. That is because it's not necessary for receiving mail with these addresses, since all incoming mail is forwarded to [email protected], anyway, and therefore immediately available in Mail.app.
The problem arises when sending e-mails within Mail.app. I can easily add all three addresses in the "Mail" > "Settings" > "Accounts" settings window by entering them in the e-mail-address-field separated by comma (e.g. "[email protected], [email protected], [email protected]“). This allows me to select the desired outgoing address on a per-message basis in the compose window.
There is, however, a problem with this: This setting means that mail from all three addresses is being sent using the same SMTP server. This can cause problems for domains that do have SPF-records, for example. Therefore, I'd very much prefer to not only select the outgoing mail address on a per-message-basis, but also the SMTP-server I'd like to use. Since Mail.app allows me to add multiple SMTP servers in the account's settings window, I believe there has to be a way to select which one to use on a per-message-basis? Whenever there's a problem with an SMTP-server, a window opens up asking me which of the alternative SMTP servers I'd like to use, instead. This indicates that this function exists – it's just far from obvious for me where to find it in a normal usage scenario.
Does anyone have an idea? Any hint is welcome!
Thanks
Nick

That has nothing to do with it. I ended up working around the problem by changing the account name.
But I still think this is a bug, so I won't mark the topic as answered (a workaround is not the solution).

HT4864 can I use the icloud smtp server as the outgoing server for all my other imap accounts?

I have several imap accounts. I want to send all my messages using the icloud server. I put the icloud server as the smtp server for each account but mail is not able to send the messages. The configuration is correct for the smtp iclous server, I checked.
Is there anything I'm missing?
Fausto

The only thing you're missing is that you can't do that. You have to use the correct smtp server for the mail accounts. Email providers generally don't like sending some other company's mail. If you want to send from the icloud servers, use your icloud account when composing.

Mail IMAP from Gmail - smtp server does not work.

I have a question about the inner-workings of Gmail IMAP as it relates to sending mail on an outgoing smtp server. When I'm at school (high school), *I can only receive mail; I cannot send it*. I talked to my computer science teacher and he said the school restricts outgoing messages because apparently people can use the school's smtp server to send spam...or something along those lines. Anyway, connecting to Gmail directly works fine, but I also had a nice setup on some shared computers for other students (who are not computer-savvy) who needed to access a single email address. Is there a way around this (albeit minor) inconvenience? Can I set up Mail preferences to use a different port or something in order to avoid the smtp restriction? Not that big of a deal, but still somewhat perturbing (and I will go to great lengths to fix it lol). Tell me if this is doable/if you need more info.
Thanks!

GMAIL's Mail 4.0 setup procedure.
Plus Google's Problem's sending mail.

How do i create a mail box in the SMTP server thru a java program

How do i create a mail box in the SMTP server thru a java program. If it is possible thru a java program.pls suggest a mail server compatible for the above possibility to work.
pls help ....

Please let me know if it is not at all possible to
create a user account automatically thru a program
(java) in a mail server... how does yahoo work
then..does he manually add a user to the mail
server...By talking to a web server not a mail server.
>
Is not there any mail server that will allow us to
create mailboxes for my java program.. how do the
other web account services work..
As I said mail servers do have management interfaces. You need to find one and then determine what the management interface is.

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

Importing Windows Outlook 2007 email to Mac Mail using Thunderbird Workaround Looses Some Messages

After being away from using a Mac for 5 years I'm back with an iMac.
I found this workaround to import Outook 2007 emails to Mac Mail using Thunderbird on the PC http://www.trickyways.com/2010/08/how-to-transfer-emails-from-outlook-to-apple-m ail/
On the PC Thunderbird imports all my Outlook messages correctly and all are there.
Then when I import the resulting Thunderbird mailboxes to Mac Mail some messages are being lost. The directory structure for my mail folders imports correctly, just that some messages are missing.
There are earlier posts here saying Eudora Mailbox Cleaner worked for people but this wont run on Mountain Lion.
So has anybody got any ideas on how the get all my Outlook e-mails to the Mac without losing anything?
What about software like Outlook2Mac, does it work fully or will I still have the same issue of some lost mail?
Can't believe I am having this problem migrating Window to Mac, you'd think it would work perfectly and not put people off from switching.
Cheers.

Okay I slept on it and had a brain wave.
I set up iCloud Mail on Outlook 2007. Then copy messages from my Outlook Inbox to iCloud Inbox.
On the Mac copy the messages from iCloud Inbox to a folder On My Mac so they never get lost if I delete the iCloud account.
Playing about with it and it seems to work fine. Any reason why it could cause issues?
I love it when a workaround comes together!

Ipad 2 suddenly decided it couldn't send mail on mobile me smtp server any known fixes

Ipad 2 suddenly decided it couldn't send mail on mobile me smtp server any known fixes?

iOS: Unable to send or receive email
http://support.apple.com/kb/TS3899
Can’t Send Emails on iPad – Troubleshooting Steps
http://ipadhelp.com/ipad-help/ipad-cant-send-emails-troubleshooting-steps/
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http://www.apple.com/support/ipad/mail/
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Mac mail: Use SSL on SMTP Server turning on

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