Outgoing mail collecting in Outbox

Using Yosemite Mail, I have 4 email accounts, two of which are through gmail. When I send an email from my non-gmail accounts they go out promptly. When I send an email from one of my gmail accounts i starts to collect outgoing messages in the Outbox and does not send them. I have changed the gmail application-specific passwords in Preferences and even generated new app-specific passwords through Google. It will only send if I shut Mail down and restart it.
It appears that Mail was changed in Yosemite to be more picky about the format of the Preferences page.
Has anyone else seen this? Do you have a work-around? I am currently not sending anything from my Gmail accounts (no problem receiving emails there.)

Each Gmail account must have it's own app specific password.
Note: OS X 10.10.3 will have improved two step authentication for Gmail support. See: http://9to5mac.com/2015/02/06/os-x-google-2-step/
the Public beta for OS X 10.10.3 was released today so you should see this soon as an update.

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TS3276 Gmail outgoing mail stuck in Outbox-please help

I have several Gmail accounts and one particular account is putting all of my outgoing mail in the OUTBOX when I send from my Macbook Pro, but not from my iPhone.
How do I fix this?
Thanks!

Are you using mail.app?
Have you tried going to Message in the Menu Bar and selecting "Send Again" ?

Outgoing mail stuck in outbox

I can receive mails but outgoing mail stuck in outbox.
checked mail preference and changed outgoing mail server (SMTP) to iCould (iColud). still does not work.
what else shall I check?

Hello Lilikoii,
Thanks for using Apple Support Communities.
From your post I see that you're unable to send email using the Mail application on your Mac. To troubleshoot this issue please follow the directions in the article below.
If you can’t send or receive email on your Mac - Apple Support
Have a good one,
Alex H.

Iphone 4 outgoing mail stuck in outbox

I have an iphone 4, which I love. I have 4 accounts on my email. All 4 receive email. All 4 send email. But only 3 send email as a reply. The 4th sends it for ever to my outbox and says my account is not recognized by the server. Even tho I didn't have to do it for the other 3, I found that by adding @comcast.net to my email name on the outgoing mail line, it worked. The one that hadn't been working had a longer name than the rest. Perhaps that had something to do with it.

i would love to post to your cited forum, but cannot find it in the directory
even mail application is not in the directory
when i click on your link i come directly back to what i suspect is the os 10.7 oper sys forum.
more info please
my posting
no issues until recently when the incoming mail from my internet providers primary mail box, [email protected], does not always show up in my "primary" mailbox. it does show up in the aggregated "inbox" mailbox. i have done a mail box rebuild to no avail. have preferences been changed? - have i inadvertantly changed them?
i am now running os 10.7.5 and mail version 5.3. verizon fios is my internet provider.
about the time of the issue start, i renewed verizon fios with the same features and services, but the internet speed increased substantially. i did not change any fios adaptations or preferences - to my knowledge.

Outgoing mail sits in outbox on Macbook Pro

On the MacBook Pro, OS 10.9.5, mail stopped going out from all three accounts. Incoming mail is fine. Connection Doctor says connected. Checked the settings with one of the accounts and are correct. Does anyone have a solution? It seems to be Mail related. Thanks.

Usually it's a password issue with SMTP.
EDIT SMTP SETTINGS
In Accounts window > Outgoing Mail Server SMTP: select to Edit SMTP Server list... from popup.
Select account in the list.(It's not uncommon to find extra SMTP servers listed. When you remove account, Mail does not delete the smtp info. You might need to do some clean up in the list to remove the extras.)
Under Advanced Tab:
Apple defaults to the default ports (25,465, 587) but some servers prefer a custom port. Check to see what port they recommend. Gmail for example likes 465, Outlook.com 587, Comcast 465
(note: Mail really likes to default to 587 in Yosemite now. Try entering 465 and see if that helps)
Verify if your server require SSL.
User Name. Enter full email address eg. [email protected]
Add password if it is blank.
Open Connection Doctor under Window in the Menu bar.
Do you see green light now for your account SMTP?
Comcast IMAP Settings:
Incoming server: imap.comcast.net
Outgoing server: smtp.comcast.net
Authentication ON
Incoming Port: 993 with SSL ON
Outgoing Port:
465 with SSL ON

Outgoing mail stuck in outbox, why?

How do I get my mail out of the Outbox?

OS X Mail: Troubleshooting sending and receiving email messages

From time to time, my outgoing mail messages get stuck in the "outbox". I'm having trouble resolving the problem.

From time to time, my outgoing mail messages get stuck in the "outbox". I'm having trouble resolving the problem.

I use Comcast. My computer (Mac Air) also uses my iCloud and Me accounts. The message I get back says they are all offline.

TS3899 Outgoing Mail goes into an outbox. I cannot access it

I have tried everything the help communities suggest. Nothing works. Nearly every day something winds up in the outbox for no discernible reason. How can I access mail in the outbox, edit it and send it? Judging from the number of questions about this problem on the websites, it is a common problem. Most of the time there is no answer to the questions posted about this problem. I have had no luck asking Apple Support.

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/
Setting up and troubleshooting Mail
http://www.apple.com/support/ipad/assistant/mail/
Server does not allow relaying email error, fix
http://appletoolbox.com/2012/01/server-does-not-allow-relaying-email-error-fix/
Why Does My iPad Say "Cannot Connect to Server"?
http://www.ehow.co.uk/info_8693415_ipad-say-cannot-connect-server.html
iPad Mail
http://www.apple.com/support/ipad/mail/
Try this first - Reset the iPad by holding down on the Sleep and Home buttons at the same time for about 10-15 seconds until the Apple Logo appears - ignore the red slider - let go of the buttons. (This is equivalent to rebooting your computer.)
Or this - Delete the account in Mail and then set it up again. Settings->Mail, Contacts, Calendars -> Accounts Tap on the Account, then on the red button that says Remove Account.
 Cheers, Tom

Mail Sending and Outbox errors

I tried to look through old threads and find an answer to my question, but I haven't really read anything about how to fix this problem. I set up my Mail at the beginning of the summer when I got my MacBook with info for my Gmail email account. Everything was fine and I was able to send/reply/forward messages to other people. However, I just started school at UMBC and at first I was able to send. However, for the past two days my sent messages are not being sent and are being clogged in my Outbox. When I check my preferences, I see that my outgoing mail server reads "Gmail (offline)". I'm still getting incoming mail, but I'm not sure how to fix the "offline" problem. I've tried restarting the program and my computer, but the same keeps occurring.
The only thing I can think of is that to use UMBC's internet, you have to go through the intranet login pages first. I'm not sure if it's causing it or not, but it's becoming very inconvenient for me to have to open Gmail on the web and send my messages through there rather than through Mail.
Please help if you have any ideas! I'll keep checking the thread so I can provide with further information if needed.

Okay, I got mine to send (still shows as GMail Offline, though). Found this fix on the thread
http://discussions.apple.com/thread.jspa?threadID=1685517&tstart=30
The post by Nathan C. (the rest of the thread was not helpful).
The solution seems to be to set the outgoing mail server (smpt.gmail.com) port to 587 instead of 25.
Hope this helps you too!

Just changed outgoing mail server now unable to Send to old contacts

Please see error message below:
"This message could not be delivered and will remain in your Outbox until it can be delivered.
The server "smtp.snet.net" did not recognize the following recipients:"
These however are all address that I have previously mailed to and are suddenly not working.
Thanks for the help. Please reply to [email protected]
Karen

Howdy andy237,
The article linked below details how to go about using Connection Doctor in Mail to determine the cause of your outgoing mail servers being offline, as well as detailing methods for resolving the issue.
OS X Mail: Troubleshooting sending and receiving email messages
http://support.apple.com/en-us/TS3276
Cheers,
Allen

Outlook 2013 with Exchange 2013: Mails stuck in Outbox

Hi everybody,
I am using Outlook 2013 connecting an Exchange 2013 server. After sending a mail, all outgoing mails remain in the outbox. After removing the cache files it works for a while until the problem occurs for the next time (approx. once every two days).
I already re-installed Windows 8 to test it on a completely clean environment...OWA works fine, the problem only exists with Outlook.
Additional note: It might be interesting that after sending a mail, the "Send/Receive progress" window states "sending [email protected] - complete" but the Mail is still in the outbox and was not delivered to the recipient. Safe mode doesn't work
for me. Other users connecting with Outlook 2010 don't have a problem with this exchange server.
Do you have any ideas? If I can provide you with further information, please let me know.
Greets,
Basti

Thanks for your answer. Here are the requested information:
>What addins are you using?
No 3rd party addins, at the moment "Microsoft Exchange Add-In", "Microsoft VBA for Outlook Addin",
"OneNote Notes about Outlook Items" and "Outlook Social Connector 2013" are activated. But the problem also occurs if no addin is active (or even in Safemode).
>Antivirus
scanners can prevent Outlook from moving messages to the sent folder.
I will try to deactivate the virus scanner the next time. (Avira is used)
>Can
any address trigger this behavior or does it happen with certain addresses?
No, it does happen with any address by random. Once the problem occurs, I can try to send as much mails as I want to
any address - nothing leaves the outlook client.
>Is
this your mailbox or a shared/secondary mailbox?
It is a user's mailbox, nothing shared.

Why is Outgoing mail from my iPad not appearing in Outlook 2010?

I have set my iPad to synch with my gmail account. In turn my gmail account downlaods and synchs with Outlook 2010 on my Windows 7 PS.
Everything works except that when I send mail from my iPad or reply to incoming mail from my iPad, my replies, whilst synchronising with my gmail account, and showing in the Sent folder in gmail, do not download to Outlook.
If I log into gmail (from my email or via Safari) and send mail direct from gmail these messagesshow in the Sent box and DO show in iPad gmail outbox and Outlook, though they show in the Outlook inbox!
So the only mail that gets stuck in gmail and won't download to Outlook is outgoing mail sent from gmail in my iPad.
I can work around this by sending a bcc to myself of every outgoing message I send from iPad. In this case the Send copy shows up in the Sent folder in gmail and does not download to Outleook but the bcc copy arrives in nthe Inbox in gmail and does download to Outlook. Its ugly but works.
A proper fix would be better - does anyone have any ideas?

For Exchange GMail there is a way to set your iOS device to use a different "Send As" name than when using a computer. Unfortunately in your case, you can set your computer to send an alternate name but the iOS device can only send the default GMail name, which is the name associated with your account. Ideally, you would like your iOS device to use the alternate and let your computer use the default.
But if you want to play around with this ...
1- On the iOS device itself, use Safari to navigate to m.google.com/sync. You will have to log in at the prompt with your GMail account info.
2- Select the iOS device name (in case you have multiple iOS devices using Google sync).
3- Select "Enable 'Send Mail As' for this device" and Save the changes.
4- Using a computer, log into your GMail account and select Settings/ Accounts and Import, then at the "Send mail as" prompt select "edit info" (off to the right).
5- Change your outgoing name.
The name you specify in #5 will be used by your computer, but the iOS device will continue using the original (default) outgoing name. You can see why you need the opposite in your case, so unless you can change the default to be your wife's name and then set the alternate to be your name, I think you're out of luck.

Mail sits in outbox and doesn't send

mail sits in outbox and doesn't send

remember there is both a mail Sender and a mail Receiver. Receiver setup information is easy to find, but Sender setup information is a little harder to find.
Use exactly the settings your ISP provided, or use this Apple Mail Setup Assistant. (rest assured, Apple does not use this to collect your email address.)
https://www.apple.com/support/mail-settings-lookup/
The easy-to-see info in Mail preferences is for your Mail Receiver. This corresponds to the top part of the box from the Apple site.
You need to use Connection Doctor and click on the red light to get easy access to the Mail Sender info. This corresponds to the bottom part of the box from the Apple site.

Why my sending mail goes to outbox?

I have tried so many ways to send email from my ipad but I am not able , all the mail goes automatically to outbox and stay there .
I turn on/off the ipad and also delete all the app in the back ground but still problem resist.
Could any body help?

Sound like the iPad is not connecting to your outgoing mail server correctly.
I had this same issue. I could only send email while at home, connected directly to my ISP.
Some mail servers require password authentication when sending while connected through other servers.
Settings > Mail > select the account.
Tap Outgoing mail server.
Enter your username and password and select Password authentication.

Outgoing mail problem

hello mac users...
having problems with mac mail, again. spontaneously, without any changes to my system, i am not able to send mail. am able to receive, and am able to communicate with the outgoing mail server (as per a check with the system administrator) but all outgoing mail is held in my out box and i receive a generic error message when attempting to send mail. i had a problem with mail before that was remedied by deleting the envelope folder from the mail library, tried that again this time, to no avail...
any suggestions?

You are able to send messages.
If a message cannot be sent for whatever reason, it will remain in the Outbox mailbox with an error message provided.
A message will not be moved to the account's Sent mailbox unless it was successfully sent by the SMTP server used by the account. Open any message in the account's Sent mailbox and at the menu bar, go to View > Message and select Long Headers.
Information in the Message ID field (ends with @mac.com or the domain for the email account provider used to send the message) is another indication the message was successfully sent.
A successfully sent message is either accepted or rejected by the recipient's incoming mail server. Due to spammers using "dictionary" attacks - guessing at email addresses for an email account provider's domain and not providing a valid sending or return email address, many ISP's and email account providers are no longer sending a return email error message to the sender of a message when a message is not accepted by recipient's incoming mail server.
If a message is accepted by the recipient's incoming mail server, what happens to the message after that has nothing to do with the email client used.
Although for the most part, messages are received in a matter of seconds but not always since successfully sent messages do not take a straight line from the account's SMTP server to the recipient's incoming mail server.
I completely reformatted my secondary hard drive, installed a
new system only and configured my mail account from scratch
and the problem is still there. I have also cleared the cache's using
Onyx, repaired permissions, even removed the battery to reset
other setting, but nothing has helped.
None of this has any effect or helps in this situation since these messages were successfully sent.
Contact your providers and ask if there is anything they can do with the Message IDs for these successfully sent messages.

Outgoing mail collecting in Outbox

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