Mac Mail, cannot send

Cannot send email using Mail 7.3. I am connecting and receiving mail, but suddenly haven't been able to send over the last 2 wks approximately. No settings have been changes, so I'm positive my smtp setting is just fine. Any suggestions?

Hey booshelley,
I'm sorry to hear you are having mail issues with your MacBook Air. If the Mail Connection Doctor is showing no issues but you are still unable to send mail, you may want to enable the more advanced display/logging options and see if anything stands out, as noted here:
Show more detail
Mail Connection Doctor can show even more detail about the connection:
Click the Show Detail button to open a drawer showing basic communication between the Mail app and your email service. If the drawer is empty, click Check Again to start another check. You can copy data from this drawer and paste it into another app for easier viewing. Messages that contain "ALERT" come directly from your email provider.
Select the Log Connection Activity checkbox to cause Mail to generate detailed logs of its communication with your email service. To view the logs, click Show Logs. To stop logging, deselect Log Connection Activity.
Use Mail Connection Doctor - Apple Support
Cheers,
- Brenden

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Attachment size - Mail cannot send email attachments over 1.5Mb

Had this issue with Mac mail for well over a year now.
Mac Mail, connected to Exchange server.
Mac Mail cannot send attachments over about 1.5Mb. This does fluctuate, sometimes its as low as 600Kb.
It seems to be related to the internet speed you have, Slower internet connections and attachment size you are able to send goes down, faster speed and it allows bigger attachments to be sent.
Im assuming its some kind of time out issue.
With Windows and Outlook on the same internet connection = NO PROBLEM AT ALL!
This means its not an exchange only problem, its specific to mail and exchange.
I have several friends all switched over to Apple in the last 2 years and ALL having the same issues and despite logging several calls with Apple and trying everything they have suggested still no fix.
I have searched around and it seems lots of people are having similar issues all with no resolution to this.
Please can someone suggest anything new that might resolve this, im happy to try anything!

@Brooksymj
We had a similar problem - but we had one Mac which had been migrated from and old G5 Tiger to a new Intel iMac Snow Leopard and no problems existed (all size attachments send), so we checked out what was different about that machine's mail.plist preferences. We spotted some obvious ones that didn't exist on a clean install of Snow Leopard, so added them, which worked for us, as follows...
1/ get Pref Setter (www.nightproductions.net/prefsetter.html)
2/ quit Mail and launch Pref Setter
3/ find com.apple.mail and double-click it
4/ click once on any one of the entries without an expansion triangle
5/ click on Actions and select Add New Array
6/ call the new array DeliveryAccounts (no space)
7/ with DeliveryAccounts highlighted, click Actions and select Add New Dictionary
8/ leave the default name of Item 1
9/ with Item 1 highlighted, click Actions and select Add New Key
10/ call the new key MaxMessageBytes (no spaces)
11/ change MaxMessageBytes class to Integer
12/ set the value to the maximum individual message size permited by your exchange server
(ours is 50MB = 52428800)
This also worked on my mbp with Lion.
Hope this works for you!
Ian

All sub-folders in Mac Mail cannot synchronize with Exchange Server 2010

Hi all,
All sub-folders under Inbox in Mac Mail cannot be synchronized with Exchange Server 2010. There are 2GB messages size in Inbox folder and 500MB messages size under Inbox's sub-folders. All messages can be sent out and received and it can work in Outlook 2007 and Outlook 2010 normally. However, all messages in sub-folders cannot be synchronized (empty sub-folders).
Does this problem relate to message synchronization order of Mac Mail with Exchange Server? Do all sub-folders messages be synchronized after synchronization complete of Inbox? The synchronization of sub-folders will not happen if the synchronization of Inbox does not complete, doesn't it?
All messages synchronization is over internet. Can anybody help?
Thanks a lot
DT1640759

Hi,
1.please check the mailbox send and receive quota for exchange 2013 migrated mailbox.
2.Please check the email attributes of the exchange 2013 migrated mailbox because it seems to be a problem with that particular mailbox.
3.Then do the message tracking and that would be the only way to find the where the send messages has gone.
4.Please check and confirm you have an enough space on the disk where exchange queue database is residing.
I think I need to create a receive connector in the 2013 to receive from 2010 ?
No need ,by design exchange 2013 cas server default frontend receive connector will be having an
entire ipv4 and ipv6 segment and anonymous connection is checked by default.
I think I also need to create a send and receive connector for 2013 users to each other?
No need , an intra organisation send connector and the default receive connectors in exchange will be used
for internal mail flow between the exchange 2013 users.
Please reply me if you have any queries .
Regards
S.Nithyanandham
Thanks S.Nithyanandham

Just upgraded to Yosemite 10.10.2 on my iMac 24 inch and now my Suddenlink POP email account won't accept messages. The message says unable to receive Mail and the warning says: Mail cannot send your password securely to the server. You can remove th

Yesterday I uploaded Yosemite 10.10.2 thinking it was fixed by now. In Mail, my POP account gets this error message: Mail cannot send your password securely to the server. You can remove this restriction in the Accounts preferences by setting “Allow insecure authentication”, which could put your password at risk.
My provider says it's an Apple issue. The gmail accounts are logging in fine. Any help? Something simple?
Thanks anyone.

Thanks Csound1. That did work and Mail was able to connect to the internet. Green light status. Is it because of my provider that I may never have had secure connections? Is that an Apple thing or do PCs have the same issues? Appreciate your help. I'll research insecure connections as I am ignorant of the consequences.

Loaded Yosemite onto mid 2011 MacBook Air. IMAP account goes offline - message - Mail cannot send your password securely to the server. Allow insecure authentication doesn't work. Repeated reloads. No joy. Help!

Mail cannot send your password securely to the server. You can remove this restriction in the Accounts preferences by setting “Allow insecure authentication”, which could put your password at risk.

I have the same problem.
Late 2012 imac 27", intel i7 core
When I upgraded to Yosemite, suddenly my email account (netvigator POP) gives an error:
Mail cannot send your password securely to the server. You can remove this restriction in the Accounts preferences by setting “Allow insecure authentication”, which could put your password at risk.
I have shut down & restarted mail, but no success. If I select Allow insecure authentication, it works, but that's not a long term fix.
I also have a hotmail POP account enabled, and that is working fine.
What's happening Apple??
(Long term apple family - iMac, iBooks, TimeCapsule, iPhones, iPads, AirportExpress etc etc)

Mac mail keeps sending emails from different accounts even though it says correct email in "sent" folder. Recipients reply and it goes to different email address. So confusing.

mac mail keeps sending emails from my different accounts even though it says correct email in "sent" folder and correct email account was highlighted. Recipients reply and it goes to different email address. So confusing and annoying.

Hi Mike,
I had the same issue and managed to solve it.
Go into Mail>Preferences>Accounts
Then in the account information tab, at the bottom should be outgoing mail server (SMTP) and click the drop down box
Mine had a few different servers in it so i went into edit SMPT server list. Click advanced and it will tell you which ones are going from which email address.
Delete the ones you dont want, and it should work or instead of deleting click use only this server, i imagine that will work to
Hope This Helps
George

When I am sending one message, mac mail shows sending several (6 last time), is it virus?

when I am sending one message, mac mail shows sending several (6 last time), is it virus?
mac mail also freezes from time to time and closes for no reason

It is not a virus. It's a bug in Mail that fails to reset that count, so it keeps incrementing each time you send a message. When it says it's sending 6 messages, that really just means you're sending the 6th message since you last opened Mail.

POP3 Business E-Mail CANNOT SEND HELP PLEASE

POP3 Business E-Mail CANNOT SEND HELP PLEASE
PLEASE HELP I have two business email accounts an cannot send with either. Just lost a big contract because I answered contract questions and then I find out it did not send 3 days later. I have always had (hide sent emails enabled on all previous BlackBerry phones) We need help. FREE HELP NOT COST PER CALL BASIS. This is BlackBerry's problem not ours.

Hey all,
If you have your network service providers SMTP server inputted and still experiencing trouble. Then we suggest contacting us so we can gather logs to find the root cause.
Please contact your network service provider and ask to be transferred to BlackBerry.
This will help us resolve this new issue.
Thanks
-ViciousFerret
Come follow your BlackBerry Technical Team on Twitter! @BlackBerryHelp
Be sure to click Like! for those who have helped you.
Click Accept as Solution for posts that have solved your issue(s)!

How do I stop Mac Mail from sending an unauthorized "out of office" message to a few, not all, my associates

How do I stop Mac Mail from sending an unauthorized "Out off Office" reply to several, not all, of my associates emails? Only happens with me.com mailbox, not Earthlink. Am not getting some important e-mail from brokerage and business associates.

If Earthlink is unaffected it is probably a settimg in me.com. Log into me.com account in a browser such as Safari (will get icloud.com) and select the settings (gear) icon bottom left, and then click on the airplane icon. Make sure vacation setting is unchecked.

Setting up mail. cannot send password securely

when i go to set up my mail with my aol account i get a message saying mail cannot send my password securely to the server. this is on the first welcome screen where you enter your name email and password.....it does give me the option to do it manually but if i do that i cannot send any email but i receive email. i checked the incoming and outgoing settings and there right..... what does this mean is there anyway to get past this
thanks

I've never seen this particular warning, but it's important to note that passwords for e-mail are always sent insecurely unless you are able to connect via SSL. You can set Mail to connect via SSL in the advanced account settings, assuming that your mail provider (AOL) allows such a thing, which some do not. Even if the password is sent encrypted, the rest of the e-mail is not, so you should never send any confidential information via e-mail, any more than you'd put it on a postcard.

OSX Mail - Cannot send message using the server ....

Hi there,
Mac Pro with OSX 10.6.
*Can receive mail, but can no longer send email* using the program Mail.
Been getting the popup "Cannot send message using the server [shawmail.vc.shawcable.net] for the past 3 days. I hadn't changed anything about my computer, and have had the Mac for 2+ years. So this just started doing it on it's own.
I had a technical support guy from my service provider even interface with my computer, where he could see my desktop right over the internet, and he couldn't get it fixed either.
I googled this problem, and found solutions like:
1. Uncheck "Use SSL" (Done that, and it was never checked "on" to begin with)
2. Make sure Authentication is set to none, with no password (done that, and it wasn't set with a password to begin with)
3. Delete [user]/Library/Preferences/com.apple.mail.plist (done that, didn't do anything)
4. We even totally deleted my account, and started a new fresh one. Didn't work
The tech support guy did show me a way to email online, using the same email account. That worked, but it's a hassle to go onto a web-based email program -- it's not my preference. So, with great certainty, it's not my service provider, because I was able to send emails on this web-based email program using my email account.
So there, I'm stumped.
Hopefully someone can help. What's bizarre is that googling this problem, I have found many other people that say it happens arbitrarily, out of nowhere.

I can't believe how ridiculous this issue is. i have been searching for days for a solution to this. i have tried EVERY recommendation on these forums and nothing works. It appears that this issue dates back to TIGER. I had this problem back in January and just bagged figuring it had something to do with iweb. I bought a new html program and was able to send out my newsletter last month no problem. Suddenly, one month later- here i am again, unable to send out my newsletter with no help from Apple or verizon, or these forims, or anyone else. To think that a company that I have stood behind and loved so much can't be be bothered fixing such a simple issue that has been going on now through 5 OS's (I am using Lion but I had the issue using leopard as well) is a disgrace.

How can I use Mac Mail to send a delayed mail?

I am trying to send a delayed email, meaning the email is not sent immediately
when the send button is pressed but at a pre-determined time.
I have looked through Google, tried different third party scripts available, including
Mail Scripts 2.10.3 by Andreas Amann, but none is supported under Mac OS X Lion.
I believe Mac Mail itself does not support this feature (to my disappointment),
but I read about using iCal and Automator to do my intended purpose.
However, I am not familiar with script-writing. If someone can provide me a
step-by-step procedure OR give me another way to do my intended purpose,
it will be highly appreciated.

I opened Airport Utility today and it appears to have been simplified to the point where you can't do much with it these days.
Yes, welcome to the Fisher Price toy box utility.. where nothing in the way of advanced usage is offered.
Is there a way to accomplish what I want to do that is reasonably simple?
You can put time controls onto the offending addresses.
But if the hackers know anything at all they know how to access the MAC address of the computer and change it.. so the effectiveness of this is limited.
Change the current setup and password.. You must use WPA2 Personal and I recommend you use a pure alphanumeric password, mix case and numbers of 20 characters or more for your situation.. do not give that password to anyone.. protect the admin password of the TC itself equally well but with a different password. And protect the physical access to the TC from anyone in your home.. because the fact is all security on the TC is an illusion if the TC has open access.
See how to find passwords here.
i forgot my password for my router, how can I change them.
So anyone can discover your passwords without your knowledge and leave no trace on your system.
If you make no progress.. I suggest replacement of the TC as the main router of your network.. you need something with controls.. and even better controls that allow you to block people.
The favourite one now is older Netgear WNDR3800 . .you might need to buy from ebay although a few new ones are still around.. alternatively the WNDRMACv2 is simply the same hardware in a white box.. instead of black.
Load gargoyle firmware onto it.. sorry if I even point to where you can find this info my post will be deleted.. I can say it.. just cannot help further.. so use google.. there are lots of posts and let me assure you this get combo.
You can continue to use TC at what it does best.. a dumb wireless AP and location for TM backups.

Mail cannot send out

Normally I using mail is no problem just last few week the email cannot send out. But receiving still ok. This morning I use iPad recevied, send mail instead of Mail from MacBook.
In the same time I also try to use office mac (outlook) is same receive is ok, cannot send out.
The questions what happend on mail or outlook on MacbookPro? Since iPad, iPhone can using mail (receive, send) is normal.
Angie,

The sever did not changed, if they changed why iPad can send-receive as normal? Only happen on Mac. Last night I try to use office Mac (Outlook) is same receive mail is ok but cannot send out.
What can I do? I should re-install again for office Mac? Or Mail? (how to reinstall mail?)

Mail cannot send

using the mail application my emails will not send.
it keeps saying "cannot send message using the server .mac (mobileme) connections to the server "smtp.me.com" on the default ports timed out"

nvm i fixed it! for those who need help this is how i fixed it....
http://help.yahoo.com/l/us/yahoo/mail/classic/mailplus/pop/pop-14.html

Mac mail cant send email

my mac mail rejects the ISP Cox providers server when we go to send email. We can receive email just fine. I have deleted and re-input all the correct incoming and outgoing server info and still not able to send email
Any suggestions?
mac mail v 3.6

hokie8t9 wrote:
my outgoing settings are smtp.cox.net. I also noticed with my new laptop, which is windows based, it cannot send emails on the cox isp network either. Cox insists it is not their firewall or network as we can receive email fine. thanks for your interest.
That is the name of the server, it is not the settings for the server, those are linked to below, if your settings are different your mail won't work correctly
Cox Mail Settings

Mac Mail, cannot send

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