Two Google mail accounts in Mail cannot send properly

I recently added a business email that was set up through google mail to Apple Mail. Both boxes receive mail fine. However, when I try to send from my business email it is delivered through my personal. When I try to edit the outgoing server to differentiate the two accounts Mail gives an error message that it cannot connect & defaults to online. I have tried numerous options with no success. Ironically, the emails perform perfectly on an Iphone but not a Macbook Pro. Any thoughts? Thank you

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I have two google mail accounts, one is work, one is home. I prefer to keep things separate. On my iPad, formerly had no problem checking each account. Now when I log into either account, my poor iPad acts like its spinning its head.

I have two google email accounts - one is personal, the other professional. I like them being separate. Until a few days ago, my ipad could pull up either account I needed at the time. Now, though, when I try to pull up either account after signing in, the line above the blue line (sorry I'm new to this and don't know the terms) switches rapidly between the two account names and nothing appears below where the mail should be. What do I do? Thanks

Update to above question:
Hello All,
To anyone with the same problem described above, on THEIR iPad (if it is running iOS 7.0.2):
Go to Settings; Mail, Contacts, Calendars; DELETE your *******@btinternet.com e-mail account, that you originally set up either using 'Other', or the 'BT' option which I am sure was in the list previous to the iOS 7 update.
Then ADD a NEW account choosing YAHOO from the list of options. DO NOT USE 'OTHER'.
Enter the correct details just as you (almost certainly) had already done in your previous attempts using 'other'.
When you see the 'verifying......' and 'the blue ticks' you should be able to exit settings and open your mail app and then receive all your 'old' e-mails again, AND be able to SEND as well.
All my 'old' e-mails, were NOT found in the 'old e-mail' folder though. THEY are still in my inbox.
So this fix worked for me.
After I deleted my account from 'OTHER' and put it in Yahoo, I like other people also ended up with more folders.
I hope this works for you on YOUR Apple devices.
Bob

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)

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)!

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.

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

Mail cannot send to any account!

Snow Leopard has broken my long-term Mail system!
I note that fairly recently I had problems with Mail (under 10.5) that meant it only did outgoing mail on one of two commonly-used servers. This was fixed by restoring an old (pre-problem) version of Mail prefs. Thunderbird and Eudora worked fine with identical server settings.
http://discussions.apple.com/message.jspa?messageID=10039384#10039384
Well after installing 10.6 NEITHER of my accounts will accept outgoing mail! One still shows no reason ("cannot send') the other claims that the outgoing address is rejected (oh no it isn't - the university system does not check). Incoming mail is fine.
Again Thunderbird works just fine for both outgoing and incoming mail (also under 10.6). Restoring pre-problem prefs no longer helps.
Any suggestions? (other than dumping Mail and using Thunderbird!!)

I got my outgoing Mail working in Snow Leopard. Here's how...
Since I have a cable modem, Cox does NOT require Authentication when sending via Cox's smtp server. A Cox representative told me this. Cox's servers can "see" my authorized cable modem and the servers KNOW that I am a legitimate user of their smtp server. So, no outgoing mail software-based Authentication is needed. Because of that, I have NEVER had to turn on Authentication for smtp outgoing mail. NEVER!
Well, Apple's Snow Leopard Mail has changed SOMETHING that is giving Cox's server fits. Apparently, Apple has decided you HAVE to use software-based smtp Authentication whether you want to or whether your ISP requires it, or not!
So.... to get my outgoing smtp mail working again, for each of my accounts, I had to individually set up smtp settings WITH Password Authentication turned on. Of course, it's the same password as I use for checking mail on each of those accounts. But, once I got smtp Password Authentication turned on, I'm back to being able to send Mail.
I'm sure the changes Apple made to Mail are all about improving security, etc. But this is really a bunch of BS. They have just inconvenienced a BUNCH of customers. If my ISP doesn't require Password Authentication for outgoing E-mail because I have a hardware connection that verifies who I am (that I'm a customer), then Apple has no business FORCING the Password Authentication for smtp!
This is about as dumb a thing I've seen Apple do in quite awhile!
Mark

I try to send emails after I have recieved. They are hotmail accounts. message says"cannot send mail and error occurred delivering this message. I have tried deleting and restarting. I have tried shutting phone down completely and restarting. no help...

I am trying to send emails via a hotmail account on my i phone 5 and get the following message despite recieving e mails. "cannot send mail an error occurred delivering this message"... i have tried to restart phone to no avail. I have tried to delete and re input account to no avail. I need help

Hello lclaunch22
You may need to validate the account with Hotmail. When logged in to the Hotmail account on a computer, there are instructions on how to do this.
iOS: Setting up Hotmail, Outlook, Live, or MSN email accounts
http://support.apple.com/kb/ht1694
Thanks for using Apple Support Communities.
Regards,
-Norm G.

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.

Mail, cannot send, reply or forward messages

I cannot send, reply or forward to any messages on my ipad 2.
Using iCloud, aol, and google accounts
Thanks

iOS: Unable to send or receive email
http://support.apple.com/kb/TS3899http://support.apple.com/kb/TS3899
Can’t Send Emails on iPad – Troubleshooting Steps
http://ipadhelp.com/ipad-help/ipad-cant-send-emails-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/http://www.apple.com/support/ipad/assistant/mail/
Using a POP account with multiple devices
http://support.apple.com/kb/ht3228http://support.apple.com/kb/ht3228
iOS: Adding an email account
http://support.apple.com/kb/HT4810http://support.apple.com/kb/HT4810
iOS: Setting up an Outlook.com, Hotmail, Live, or MSN email account
http://support.apple.com/kb/ht1694http://support.apple.com/kb/ht1694
Server does not allow relaying email error, fix
http://appletoolbox.com/2012/01/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.htmlhttp://www.ehow.co.uk/info_8693415_ipad-say-cannot-connect-server.html
How to Sync Contacts with Your iPad Using iTunes
http://www.dummies.com/how-to/content/how-to-sync-contacts-with-your-ipad-using- itunes.htmlhttp://www.dummies.com/how-to/content/how-to-sync-contacts-with-your-ipad-using- itunes.html
iOS: 'Mailbox Locked', account is in use on another device, or prompt to re-enter POP3 password
http://support.apple.com/kb/ts2621http://support.apple.com/kb/ts2621
eMail Groups - You can use a third party app that many users recommend.
MailShot - https://itunes.apple.com/us/app/mailshot-pro-group-email-done/id445996226?mt=8https://itunes.apple.com/us/app/mailshot-pro-group-email-done/id445996226?mt=8
Group Email - https://itunes.apple.com/us/app/group-email!-mail-client-attachments/id380690305 ?mt=8
iPad Mail
http://www.apple.com/support/ipad/mail/http://www.apple.com/support/ipad/mail/
Configuration problems with IMAP e-mail on iOS with a non-standard SSL port.
http://colinrobbins.me/2013/02/09/configuration-problems-with-imap-e-mail-on-ios -with-a-non-standard-ssl-port/
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: cannot send, "limits exceeded"

Aloha,
When I attempted to send my first Mail-originated e-mail this morning, I received the message:
The sender address [email protected] was rejected by the server p13-smtp.mail.me.com.
The server response was: [email protected]: You have exceeded your daily sending limits. See http://support.apple.com/kb/ht4863
I tried to send from both my iPhone and MacBook and received identical messages.
As I hadn't sent a single e-mail, how can this be?
Following somewhat old thoughts here in Apple Discussions, I called my Service Provider to see if the problem was at their end.
After a delightful 1/2 hour it became abundantly clear the problem was not with the Service Provider.
Following other somewhat old thoughts there in Apple Discussions, I tried sending e-mail from my iCloud account as accessed through a browser.
Again, cannot send e-mail. The response:
Your message cannot be delivered to the following recipients:
Recipient address: (my school e-mail address)
Reason: Server rejected MAIL FROM address.
Diagnostic code: smtp;550 5.7.1 [email protected]: You have exceeded your daily sending limits. See http://support.apple.com/kb/ht4863
Remote system: dns;p13-asmtpout.me.com (TCP|17.164.56.16|42392|17.164.60.196|25)
This problem has persisted all day.
The problem manifests both at home and where I teach.
Yes, I can receive e-mail at my Mail account, on both my iPhone and MacBook.
No, I have no other problems with my computer or iPhone.
As I rely on Mail as my primary e-mail... HELP!!!!
Any assistance would be gratefully received.

You can send mail from the same account on your other devices? You're sure of that?

HELP! My Office Mail Cannot Send Out Externally!

Hi all, recently I've upgrading/migrating to my new G5 in the office (whopee, finally!) I have transferred all my old data to Mail, settings everything etc, I can send and check email, I can log on to my office intranet and can actually surf the web, the only thing I cannot do is send email EXTERNALLY!!
Help! I have checked and even toggle some settings, e.g. in Mail account, under SMTP, use Authetication/Password etc but still no avail...
Anyone with such similar experience?? Thanks and cheers

Hi, just some updates, I have tried several methods, including the most drastic one by removing out all the Mail folders, data, plist preference files etc, and start Mail anew, creating my office email account from the ground up, and still, I cannot send out email externally - so "proving" my "old" mail data is ok, so I copied them back.
Could it be the SMTP that is causing all these problems?? Our office POP and SMTP settings are in "IP style" numbers addresses, e.g. xx.xxx.x.x
I am trying to get my IT dept to give me a new SMTP, if possible...
Here's another thing I found out when I launch Mail Connection Doctor:
It reported status Green, and Details-Connection and login to server succeeded.
But... Internet Connection Status, RED - Mail was unable to connect to the internet, click the "Assist me..." button for help diagnosing the problem.
When I continue with the diagnostic, it says "Your internet connection appears to be working correctly."
So I guess the office network/intranet has no problem connecting to the internet... but is this affecting Mail's ability to send out email externally??
Cheers

Mail Cannot Send..... Again!

Heavy Sigh....
I just installed a great new 500GB hard disk. I decided to wipe my old disk and go for a completely clean install onto the new disk. Everything went perfectly, except for Mail.
I had the same Mail problem when I upgraded from Tiger to Leopard last year. It took ages to fix. I kept a careful record of every setting I entered.
This time around, I entered everything just as it had been..... and it doesn't work again.
Heavy sigh....
OK, so, I can RECEIVE my mail from my email service provider's server. But I cannot SEND.
I try to send and up pops the following message box:
Cannot send message using the server (NAME).
The sender address (MY EMAIL) was rejected by the server (NAME).
I select Connection Doctor and both Connection/Login and Connection/Server are triumphantly successful.
So why oh why can't I send!
Ports. Me thinks it must be the ports.
So, Edit Server List/Advanced and my port is 465, just as it was before and has always been. I try the Use Default Ports option, which lists 465, along with 25 and 587. I close everything and...... still cannot send despite Connection Doctor connecting.
Well, I dunno.
Please help.
Martin

+Cannot send message using the server (NAME).+
+The sender address (MY EMAIL) was rejected by the server (NAME).+
I suddenly started having the can't send mail problem yesterday. Sometimes I was getting an error message related to STMP, other times it was exactly as you described. I followed all the directions here: http://support.apple.com/kb/TS1307?viewlocale=en_US
and those did not work. But they might, if quitting is done at the right time....
I don't know what fixed it, and I'm not sure if it will remain fixed (last night I fixed it on my own, only to find when I started up this morning that it wasn't working again), but today I followed the advice from another discussion to delete the outgoing server (in prefs/accounts/outgoing pulldown menu) and make a new one... make sure to delete all mail that is pending (anything in outbox save as draft and delete)... and to quit. In other words - follow the instructions on the support page or some of the other discussions, but quit before trying to send again. The other thing I did was do a software upgrade - there was something for airport and a security fix that I installed. Whether it was doing just the right stuff in just the right order or if it was the software installs that moved things along, I can't say. By the looks of it, this seems to be a long time issue for Apple Mail, though I've been using it for years without issue.

Mail "Cannot send message" but Thurnderbird can

Mail is giving an error message "Cannot send message using server" - on all my servers including dot mac..but Thunderbird can, with no probs...
This happpened a couple of months ago and reentering all the settings did not work so I used Thunderbird with no probs for a while..then I archived my emails in Mail and trashed all the accounts settings.
Mail worked just fine for a few weeks..then the same problem
any ideas?

Mail worked fine on a wireless connection this morning
Who is the internet service provider associated with this wireless connection?
But now we are back to no sending (the message btw is
"cannot send message using this server") on the ethernet connection
Is the internet service provider for the ethernet connection different from the ISP associated with the wireless connection?
Which server port are you using for .Mac's authenticated SMTP server with Mail and with Thunderbird?
Are any of the other SMTP servers not provided by the ISP associated with the wireless connection or with the ethernet connection authenticated and if so or regardless, which server port are you using for the SMTP servers not provided by either ISP or if the same ISP with both connection with Mail and Thunderbird?

Two Google mail accounts in Mail cannot send properly

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