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.

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AOL email cannot send PASSWORD securely to the server???

Hi, When I set up any aol account in mail, and click create, it always comes up with cannot send password securely to the server. This problem happened right after updating to snow leopard. Any one else have the same problem? Any solutions? Thanks.

For years and years most email servers accepted connections that were insecure, meaning that passwords were transmitted in plain text, and the email messages came back as plain text as well.
Now many servers encourage the use of SSL connections, which encrypts the data in both directions. Mail is trying to warn you that the SSL connection cannot be established, and therefore your data could be intercepted in transmission.
AOL's website (http://about.aol.com/faq/openmailaccess) states that they do not support SSL connections, therefore your only method of accessing your email is to use an unsecure connection.
Alternatively you could go to AOL.com (not use Mail.app) and read your email here as this will establish a secure HTTPS connection.
The best solution though is to stop using AOL and get either a MobileMe or a gmail account.
Regards,
-Ryan

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)

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

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)!

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

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..... 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.

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

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

Cannot send password with UTTSC

I am having trouble sending a username and password via the SRWC to a VMware View desktop when using the SunRay View Connector on SRSS 4.1 (and 4.2).
Whenever I try to send a username and password with the following parameters with SRVC:
-s 10.101.15.240 -d STU -http -- -u student -p northwestern -m -b -r disk:USBDRVS=$HOME/USBDRVS
I receive the following error:
[ID 702911 user.error] /opt/SUNWuttsc/bin/uttsc exited with error code 1 - exiting
with all of the command line options displayed before it.
When I remove the -u and -p, everything works fine, but I cannot send the username and password that I need to. According to the MAN page, I am using the correct syntax for sending a username and password, but it still will not work no matter what I do. Any thoughts?

The issue here is that VDM uses one-time login credentials which are passed to the VM. These are set-up on the back-end then communicated to the VDM-tools within the Vm, and to the VMD client on the front end.
In the case of the Sun Ray VDM client, after identifying the Vm and being told the one-time credentials, it invokes the /etc/opt/SUNWkio/sessions/uttsc/uttsc script. It invokes this script and passes the appropriate -u and -p options. It also passes any options given to it from the "Arguments" field in the GUI.
I believe that what's happening to get your exit code 1 is that the uttsc script is getting passed two sets of these options; the ones that you put in and the ones that the VDM clients derives.
You can try a couple of things... The first is to disable the Single Sign On behavior of View. This will require users to auth against the GINA on the host. This will also let uttsc pass the credentials on the Arguments Field. To do this you must edit the GPO for the Vie Agent. Details can be found in the View admin guide.
Alternatively, you could try editing the uttsc script above to ignore some of the invocation switches and use the -u and -p that you intend

Outgoing mail - cannot send just stopped one day

I hope this has not been asked and answered (which I'm quite certain it has). I have a business cox mail account and Yahoo plus and cannot send emails. But I can receive incoming. I deleted both accounts and put set them up again and the same issues keeps happening. In fact Yahoo is an automatic set up with mail. I am quite frustrated. Mail remains in my outbox and I get no messages regarding how or why they are not sent. They just sit there. Can anyone offer assistance? Thank you

Did you just update to iOS 6?
If so,
This seems to be a working solution for some (while not 100% success):
From Demo:
Try this.
Go to Settings>Safari>Clear History, Cookies and Data. Restart the iPad. Restart the iPad by holding down on the sleep button until the red slider appears and then slide to shut off. To power up hold the sleep button until the Apple logo appears and let go of the button.
From JaneMH:
After I plugged in my iPad to my PC and loaded up iTunes and let it sync up that sorted the problem and I am able to connect all right again

TS3276 Mail is not working. Cannot open new e-mail; cannot send mail. Connection doctor shows green dot in status column. I can't delete old e-mails to free up space.

Mail is not working. I cannot open new e-mail; and I cannot send mail either. Also, I cannot delete past e-mails to free up space. Mailbox seems to hang in general.

OS X version?

Setting up mail. cannot send password securely

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