Apple Mail can never send messages!

I have a gmail account that I view through Apple Mail. Anytime I try to send a message to someone, I get this error.
"Cannot send message using the serve smtp.gmail.com:[email protected]
Use the pop-up menu below to try a different outgoing mail server. All messages will use this server until you quit Mail or change your Network settings.
Message from : <[email protected]>
Send Message using: smtp.gmail.com:[email protected]
Options: Cancel, Use Selected Server, or Try Again Later."
Ususally, I click Use Selected Server and it works but sometimes it doesn't. First of all, it should work the first time around and never give me this message. Secondly, even after the second attempt it's not 100% reliable.
What's wrong?
P.S.

Never Mind. Fixed it.
Apple Mail users: At times, Mail may misinterpret your SMTP server settings. If you currently have 'smtp.gmail.com:[email protected]' in the 'Outgoing Mail Server:' field of your settings, please try changing the field to 'smtp.gmail.com' and saving your settings.

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Mail can't send messages

I have AT&T Yahoo DSL and my imac mail can't send messages. It says the smpt server has timed out trying to send the message on port 25.

Open Connection Doctor in the Window menu
Double click on whatever is showing as red.
Check the following settings.
pop.att.yahoo.com
smtp.att.yahoo.com
Click Advanced to enter the SSL and port info.
Both incoming and outgoing mail use authentication
Use (SSL) and SMTP port 465.
Use (SSL) and change the POP3 port 995.
Confirm the above settings before clicking OK.
Then check connection doctor again.
There is an incoming mail server and an outgoing mail server for each account.
So for each account there should be 2 servers.
Count how many servers there are set up in connection doctor.

Thunderbird works fine, Apple Mail can't send (and other problems)

I have both Thunderbird and Mail setup exactly alike. Thunderbird can send mail just fine, every time, from any location. Mail was able to send messages a few times but for the last few days refuses to send anything.
Here's the setup:
Four smtp servers
mail.bellsouth.net
mailer.louisiana.edu
smtp.coxmail.com
smtp.central.cox.net
each is setup with password SSL authentication. Each works just fine on any other computer and even on this one with Thunderbird. Apple Mail is the only problem. (and yes - ALL SETTINGS ARE EXACTLY CORRECT)
NO - port 25 is NOT the issue - it works fine with other software on this computer and others - it is ONLY Apple Mail which can't manage to connect to the servers.
I use an AirPort extreme and have reset it repeatedly. (I can usually connect to an smtp after doing so but only until Mail attempts to send) I have tried a direct ethernet connection as well. Same results.
Mail refuses to connect to any smtp server. (it connects to the POP servers just fine) Occasionally, if I retype in the smtp password, or even delete it and turn off SSL, it will connect for a short time. (until I try to send a message)
What's the deal?
I see others have similar problems, but all seem to be ISP related. In this case, I've controlled for everything I can think except Apple Mail.
A few other problems, maybe related or not:
Mail has NEVER saved any messages I have sent out in any type of 'sent' folder. Sometimes the folder appears, sometimes it doesn't, but it is always empty. And yes, the setting to 'delete messages in the sent folder' is set to NEVER. So they should all be there.
Additionally, the very FIRST note I created was saved in my Inbox as it should have been. NOT ONE single subsequent note has saved - I lost every one of them. (I also can't seem to find any means to manually save the note - how ridiculous)
Finally, though it isn't that important at the moment, when Mail can't manage to connect to an smtp server, it just sits there and tries to send forever. Sometimes it will tell me it failed and suggest another server, sometimes not. In all cases, there does not seem to be a "STOP" button or command to tell Mail to quit transmitting/receiving.
I'd really like to use this program since it integrates with iCal and Addressbook, but this is getting absurd.
Thanks for any help anyone can provide.

Who is your isp?
If it is Cox they say on their site that you have to use only their smtp server.
Other than the mailer server (of which I have no info), I question the ssl setting.
Cox specifically say to not use ssl when setting up the outgoing server.
Bellsouth do not appear to require authentication and do not use ssl either.
AT&T Help Center Online: How To: Set Up Your AT&T Email Account Using Apple Mail 2.1 on a Mac OS 10
http://help.bellsouth.net/bellsouth/asp/contentview.asp?isbrowse=true&sprt_cid=d 5442d40-acde-4d94-9192-0ae128b2ca78
"each is setup with password SSL authentication. Each works just fine on any other computer"
Are any of the other computers mac's?
You say that "it works fine with other software on this computer" - what is this other software that is using ssl and port 25 to connect to the smtp servers?
Port 25 is not used for ssl, use either 587 (standard) or in some cases 465 (non-standard).

Mail can't send messages: Doesn't allow fix the problem either: Help plz.

Hi all,
Mail doesn't allow me to send messages through my recent created aim.com account
I'm trying to fix the problem by changing smtp server configuration but it gives me the message:
"The servers marked with alert icons are in conflict and cannot be saved.
Two servers cannot share the same address and authentication settings.
Resolve the conflicts and try again."
There are no icons whatsoever and deleting any similar server won't take effect because Mail WON'T save the changes.
When clicking "ok" to save changes, Mail will throw the same message quoted above. So I have to click "Cancel"
Any idea to solve this issue?
Thank you.

http://support.apple.com/kb/TS3234

Apple Mail - Can't Send - Buttons do not respond

I have a new mac on the network,I setup a pop3 account in Apple Mail. It received fine but will not send.
No errors are reported. When I create a new message and click the send, it doesn't nothing. Same response as if I click save as draft. I have tried just changing the smtp settings but it doesn't make any difference. Any suggestions?

Are you really running Mac OS X 10.4.1, as your profile indicates? If not, then please update the Operating System field on your My Settings’s profile (and click Save), so that it accurately reflects the version of Mac OS X you’re running now. This is essential information that should always be provided when asking for help.
This problem in Mail is usually caused by some Launch Services cache or preferences corruption that affects the built-in spell checker. The following article describes how to manually reset Launch Services — the notes at the bottom of the article also provide information about the side effects of deleting each of the files involved:
Resetting Launch Services
If you prefer using a cache cleaning utility instead of following the manual procedure described in the previous article, take a look at this other article for general troubleshooting and cache-cleaning procedures. Actually, you should also verify/repair the startup disk (not just permissions), as described there:
Resolving Disk, Permission, and Cache Corruption
The most appropriate utility for this particular problem probably is Tiger Cache Cleaner, but you may also want to consider other utilities, such as OnyX, or Cache Out X, which are free. Whatever utility you choose, be sure to read this first:
Side effects of System cache cleaning
As an example, this is how you should proceed with OnyX:
1. Quit all applications.
2. Launch OnyX and enter your administrator password.
3. Go to Maintenance > Reset and check LaunchServices database.
4. Un-check any other pre-checked options.
5. Click the Execute button.
6. Restart the computer.

Apple Mail can't send or receive messages from Exchange 2010, Mountain Lion

Over the last several weeks, I have been unable to send or recieve e-mails from Exchange 2010 in a corprate environment. I have deleted and re-added the account several times, and sometimes it will fix the issue. Other times it won't. I have also tried deleting the account, clearing the cache in ~/Library/Mail/V2/EWS*, and then re-adding the account. It resolves the issue temporarily, but then returns to not being able to sync. I've tested it with a number of other users accounts on the same Exchange system, and it's working as expected. OSX is version 10.8.4 with current patches as of 10/7/2013.
The connection doctor shows that the connection to EWS is green. The activity monitor looks like it's updating the folders properly on sync.
Here is the message I get in the logs in high volume when Console logging is turned on:
*** Assertion failure in -[EWSConnection sendMessage:forRequest:], /SourceCache/Message/Message-1508/Message/EWS/EWSConnection.m:555
Received an unexpected error: Error Domain=EWSExchangeWebServicesErrorDomain Code=277 "The operation couldn’t be completed. (EWSExchangeWebServicesErrorDomain error 277.)" UserInfo=0x7fd1c9a97e70 {EWSErrorMessage=The request failed schema validation., NSUnderlyingError=0x7fd1c85106f0 "The operation couldn’t be completed. (SOAPWebServicesErrorDomain error -1000.)"}, response: (null)
          0   CoreMessage                         0x00007fff86a4a517 -[MFAssertionHandler _handleFailureWithPreamble:description:arguments:] + 141
          1   CoreMessage                         0x00007fff86a4a388 -[MFAssertionHandler handleFailureInMethod:object:file:lineNumber:description:] + 215
          2   Message                             0x00007fff8daa5a8e -[EWSConnection sendMessage:forRequest:] + 762
          3   Message                             0x00007fff8daaeab3 -[EWSGateway sendMessage:forRequest:] + 69
          4   Message                             0x00007fff8dac543a -[EWSRequestOperation executeOperation] + 110
          5   CoreMessage                         0x00007fff86a65b80 -[MonitoredOperation main] + 219
          6   Foundation                          0x00007fff92475926 -[__NSOperationInternal start] + 684
          7   Foundation                          0x00007fff9247d0f1 __block_global_6 + 129
          8   libdispatch.dylib                   0x00007fff87f4af01 _dispatch_call_block_and_release + 15
          9   libdispatch.dylib                   0x00007fff87f470b6 _dispatch_client_callout + 8
          10 libdispatch.dylib                   0x00007fff87f481fa _dispatch_worker_thread2 + 304
          11 libsystem_c.dylib                   0x00007fff9068ad0b _pthread_wqthread + 404
          12 libsystem_c.dylib                   0x00007fff906751d1 start_wqthread + 13

Over the last several weeks, I have been unable to send or recieve e-mails from Exchange 2010 in a corprate environment. I have deleted and re-added the account several times, and sometimes it will fix the issue. Other times it won't. I have also tried deleting the account, clearing the cache in ~/Library/Mail/V2/EWS*, and then re-adding the account. It resolves the issue temporarily, but then returns to not being able to sync. I've tested it with a number of other users accounts on the same Exchange system, and it's working as expected. OSX is version 10.8.4 with current patches as of 10/7/2013.
The connection doctor shows that the connection to EWS is green. The activity monitor looks like it's updating the folders properly on sync.
Here is the message I get in the logs in high volume when Console logging is turned on:
*** Assertion failure in -[EWSConnection sendMessage:forRequest:], /SourceCache/Message/Message-1508/Message/EWS/EWSConnection.m:555
Received an unexpected error: Error Domain=EWSExchangeWebServicesErrorDomain Code=277 "The operation couldn’t be completed. (EWSExchangeWebServicesErrorDomain error 277.)" UserInfo=0x7fd1c9a97e70 {EWSErrorMessage=The request failed schema validation., NSUnderlyingError=0x7fd1c85106f0 "The operation couldn’t be completed. (SOAPWebServicesErrorDomain error -1000.)"}, response: (null)
          0   CoreMessage                         0x00007fff86a4a517 -[MFAssertionHandler _handleFailureWithPreamble:description:arguments:] + 141
          1   CoreMessage                         0x00007fff86a4a388 -[MFAssertionHandler handleFailureInMethod:object:file:lineNumber:description:] + 215
          2   Message                             0x00007fff8daa5a8e -[EWSConnection sendMessage:forRequest:] + 762
          3   Message                             0x00007fff8daaeab3 -[EWSGateway sendMessage:forRequest:] + 69
          4   Message                             0x00007fff8dac543a -[EWSRequestOperation executeOperation] + 110
          5   CoreMessage                         0x00007fff86a65b80 -[MonitoredOperation main] + 219
          6   Foundation                          0x00007fff92475926 -[__NSOperationInternal start] + 684
          7   Foundation                          0x00007fff9247d0f1 __block_global_6 + 129
          8   libdispatch.dylib                   0x00007fff87f4af01 _dispatch_call_block_and_release + 15
          9   libdispatch.dylib                   0x00007fff87f470b6 _dispatch_client_callout + 8
          10 libdispatch.dylib                   0x00007fff87f481fa _dispatch_worker_thread2 + 304
          11 libsystem_c.dylib                   0x00007fff9068ad0b _pthread_wqthread + 404
          12 libsystem_c.dylib                   0x00007fff906751d1 start_wqthread + 13

My Apple mail will not send messages any more.

It will receive. I called Comcast and they said it is an Apple problem because I could send from the comcast site. I am using OS X 10.6.8 on a 4 year old 15 inch MacBook Pro. This started last evening when I tried to send a 330 kb message. I deleted that one and tried others. Nothing will send.
Kathy

Hello Maeo,
Thanks for using Apple Support Communities.
To troubleshoot this issue where you are unable to send email, please follow the steps in the article below.
OS X Mail: Troubleshooting sending and receiving email messages
Cheers,
Alex H.

How do I set up apple mail to only send messages from my address book to my inbox

I have uverse internet and use an att.net. I am getting too much junk mail from business, etc. How do I set it up where I only get mail from my contacts in my inbox?

Hello, not on 10.6 at the moment, but see if Mail>Preferences>Junk>Advanced has these setting choices...

TS3276 I can't send messages with mail 6.0 of mountain lion, because I can't desactivate the option SSL (Secure sockets Layers); it is locked

I can't send messages with mail 6.0 of mountain lion, because I can't desactivate the option SSL (Secure sockets Layers); it is locked

Hi, i am having the same problem. this is what i have noticed.
I have 2 x imac's and 2 x macbook air's
i upgraded the 2 macbook air's and 1 of the imac's to Mountain Lion, all these have problems acessing sites that require you to login .
the one remaining imac is still running lion and works perfect.
i am using a dlink router with DD-WRT firmware, i tested teathering from my iphone and i can log into websites fine using the newly upgraded mac's.
It's not a wireless issue as my imac is using an ethernet connection.
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Can't Send messages using mail on Bell South DSL

My parents are using Bell South DSL and a Net Gear Wireless Router. I have a Linksys Wireless Router living in GA and everything works fine. Any ideas what is going on here?
I receive all my email, I just can't send messages.

Ernie,
Greetings! I found this thread after trying in vain to set up my mom's email, which also stopped working with Bellsouth after the upgrade to 10.5 (now on 10.5.1). Email conversion was fine, and she, like others here, could receive mail but not send it.
I have followed the directions here to the letter. Still no such luck. To clarify, mail.bellsouth.net, port 25, no authentication is the only entry in her outgoing mail server list (and it's selected). Moreover, when she checks Connection Doctor, it passes with flying colors - even connecting for outgoing email.
Still pondering this one. I'm about "this close" to getting her a Gmail account (which I tested using my account - and it works fine, even IMAP). Of course if she can keep her existing account I think she'd prefer that, but I say go with whatever works ... !
Other troubleshooting thoughts welcome!
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I can not receive messages and i can't send messages also if someone rings me it, it rings at their end and then goes to voice mail but nothing at my end

i can not receive messages and i can't send messages also if someone rings me it, it rings at their end and then goes to voice mail but my phone doesn't ring

Talk to your carrier. Sounds like something is not provisioned right on your account.

Mac mail can receive but can't send messages

mac mail, can receive messages, but can't send messages. The sent symbol just spins around, but does not send.

I am using Mail 7.3, on OS X 10.9.4 (i.e. latest as of Aug 2014). I have 4 email accounts, all with their own SMTP servers. All stopped sending email at the same time.
Taking the hint from your suggestion, I looked in Mail > Preferences > Accounts, and all the SMTP servers were shown as offline (this must be a Mac Mail bug). All accounts appear to be Online under Mail > Mailbox (pulldown), and are also Online if one highlights the Inbox account, right click.
The trigger for the bug, in my case, was adding a new email account, and when Mail could not access it, it took everything offline. Removing that account did not solve the problem.
After spending hours trying all sorts of alternatives, I found the way to solve the problem was to delete all the outgoing mail servers, and reenter the information (the same information).

Apple Mail won't send invitations when initially closed

I just started using iCal to send invitations for appointments through Apple Mail. When Apple Mail is opened already when I create the appointment and click Send in iCal, it works fine. The mail is sent and delivered to the appropriate address.
But if Apple Mail is closed initially, the application starts and the invitation is queued up in the Outbox but is never sent. I can manually open up each invitation in Mail and send them individually, but why is the behavior different? Whether Mail is opened or closed when I send an invitation, it ought to deliver the invitation automatically. By not being sent, I may not realize the invitation hasn't been delivered, making the process very error-prone. Is there a way to guarantee the invitation actually gets sent without having to check the Outbox every time?
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ronright wrote:
Since I bought a new modem/router (Netgear n600), my Apple mail won't send e-mails. It will receive. My ISP is AT&T & the email accounts are via yahoo. I have a Macbook Pro with a recent OSX.
The most recent OS is currently OS 10.8.3. Your system profile confirms you are still using Mac OS X (10.7.5). If this is incorrect, please correct your profile so that you will get the correct troubleshooting suggestions/solutions.
Also, post in the OS/Mail forum of whichever OS is currently installed on your MBP. It's where the OS/Mail expert helpers hang out at.

Mail can't send email from 123-reg accounts

Hi all,
I've got an issue with Mac Mail can’t send email from 123-reg accounts.
I know there is a lot of articles on simular matters and some I have tried out with no luck, others are just speaking a whole other language.
Any help would be greatly recived, here's my situation below:
Running a iMac 2.8GHz Intel Core i5 on OS X 10.8.3
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I then decided to check if it was a problem at 123-regs end and attempted to log into web mail. This worked and was able to both send and receive emails so eliminated that possibility.
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I’ve tried out some of the articles I’ve found on here (the ones written in plain English) still no results. I’m not very IT illiterate and just wondered if anyone else has got any ideas, whether there is something specific with 123-reg accounts and Mac Mail?
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Thanks
I just had another hunt around looking at posts and discovered that it was because I recently changed to BT Infinity and they had a block on.
I didn't even think to question the ISP.
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Can't send message on AT&T - won't connect to server. Anyone else having this issue?

All of a sudden I can't send messages on my AT&T account. I get a message that Thunderbird cannot connect to server (STMP). Called AT&T and they verified all the settings; I can access my email account on Apple Mail and through Yahoo (AT&T's email provider) yet I cannot send messages on Thunderbird. I can receive but not send.
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https://support.mozilla.org/en-US/kb/cannot-send-messages

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