Apple mail cannot send

I have used Apple mail in the past with my Verizon account. I recently upgraded to OS 10.8.4. Since then, I cannot sent mail. Connection doctor says incoming and outgoinng is OK. What do I do to get mail working again?

Check the account settings to make sure they weren't altered.
in - pop.verizon.net SSL enabled port 995 password
out - smtp.verizon.net SSL enabled port 465

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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

When I send an email from Apple mail, it send inbedded links, not embedded, my font shows as plain text and signature sends as attachment??

When I send an email from Apple mail, it send inbedded links, not embedded, my font shows as plain text and signature sends as attachment??

inbedded is not a word.

New iMac: Thunderbird works OK but Apple Mail cannot receive

Just bought iMac in July 2010. Thunderbird email sends/receives fine, but Apple Mail v4.3 does not receive emails. Apple mail will send, which is received by Thunderbird. Incoming Mail Server settings good, and default mail reader is Apple Mail. Help please!

Helix13 wrote:
Just bought iMac in July 2010. Thunderbird email sends/receives fine, but Apple Mail v4.3 does not receive emails. Apple mail will send, which is received by Thunderbird. Incoming Mail Server settings good, and default mail reader is Apple Mail.
Welcome to Apple's discussion groups.
Does Mail's "connection doctor" (Window -> Connection Doctor) show you anything useful? Have you checked Mails preferences in Accounts panel, Advanced tab, to verify that things like port, SSL, and authentication are set correctly?

TS3276 Apple Mail cannot find replies or forwarded emails -- the little arrows on the left of the list of emails: "Mail was unable to find your reply to the message '[subject of message]'. You may have deleted the message." I did not delete the message.

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Of course they're in my Sent folder. Then why can't Apple Mail find them?

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)!

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apple mail not sending via my server hotmail. Please help

How would you like us to help when you don't provide any details. We don't have a crystal ball.

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.

TS3276 Someone who receives my mail sent from Apple Mail cannot receive attachments or read my email even though they are on a Mac using Safari. How could they be using Safari to receive or read my mail?

Someone who receives my mail sent from Apple Mail cannot receive attachments or read my email even though they are on a Mac using Safari. How could they be using Safari to receive or read my mail?

You can lead a horse to water, but you cannot make it drink. This person receiving my email, while on a Mac with Safari is reading their mail through Safari using Horde--our recent discovery. Why they chose to do that in unclear. The last email we sent, however, was miraculously read and received and the attachment was viewed with no problem after we told them our mail was coming from a Mac thriugh Apple Mail. It seems that telling them that our emails were coming from a Mac and using Apple Mail was enough to make them think that perhaps THEY were doing something not quite right. Thank you both, Level 7 and Level 5.
But thank you especially for the meteorologists in the UK for putting forth the correct routes for Sandy these last days, you probably saved a lot of lives.

Apple mail can send through gmail, but thunderbird cannot

I have apple mail setup and working both with a POP3 account and gmail. I installed Thunderbird. It works fine with POP3 both send and receive. Gmail not so good. I can receive emails but not send. I setup outgoing smtp as: smtp.gmail.com; tried ports 25, 465, and 587; authentication method is normal password; connection security is SSL/TLS.
This can't be a network issue if apple mail works right? I did notice apple mail is set to default (25, 465, 587) and I am guessing it will try all three.
I followed the troubleshooting page, I cannot telnet to port 25 but I get responses from 465 (connection refused by smtp.gmail.com) and 587 (appears to log in or something).
So, what is wrong?
my system:
Mozilla/5.0 (Macintosh; Intel Mac OS X 10.9; rv:24.0) Gecko/20100101 Thunderbird/24.3.0
Application Build ID 20140131124303

Do you get any detailed error message information?
Google's online help page ([https://support.google.com/mail/troubleshooter/1668960]) lists these settings for the outgoing mail server:
Server: smtp.gmail.com
Use Authentication: Yes
Port for TLS/STARTTLS: 587 ''(I think this is preferred)''
Port for SSL: 465
For your account name (user name) you need to include the @gmail.com part (this various from service to service).

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.

Huge problem using apple mail while sending email to a group...

Hey - I am quite confused... apple mail has huge problems using groups with about 150 addresses when writing and sending an email... the writing of emails is nearly impossible. Once the group name is inserted in the addressline (address book in iCloud!), apple mail uses nearly 100% CPU and further writing is nearly impossible. When sending such an email, all addresses are suddenly visible - though the box is NOT checked and the addresses should be hidden... what can I do? I use this feature (sending mails to groups) on a daily basis and cannot accept visible addresses...
Greetings and sorry for inconvenient english...
Christof

How about next time you send to the group, cc yourself, or include yourself in the group. Then receive the email on the iphone, you can "reply all" in order to send to the group. If you use an imap account, you can make a new folder, call it something like "groups", and save different group emails there for the next time you need to "reply all".

Apple Mail cannot encoding issues (Chinese Asian Language)

I've abandon Mail for almost 2 years, 2 issues I had before is the 'disappearing mail' and the encoding problem.
Now with my new MBP 17" I decided to use Mail again. I am getting the encoding problem again.
Things I tried already:
1. set the default encoding using Terminal to "BIG5"
2. check under 'Composing' preference for 'Plain Text', uncheck 'use the same message format as the original message'
3. Tried manually setting the encoding before sending. But in few instance Apple Mail tells me that there is an Error and cannot change the encoding. Even I succeeded in changing the encoding, there is no guarantee that the other side can read it properly.
This usually happens when I 'reply' or 'forward' a Chinese email to someone. So far it happens to the HTML type email.
Still I am getting problem sending mail that Outlook can properly decode by itself. To fix this from the Oulook side, they need to open the message by double click, select encoding for the message, and pick either UTF-8 or BIG5 (if the message is BIG5, select UTF-8 and vise versa) then the message will display properly.
I know this could be an Outlook problem (probably is) but I cannot tell my customer to change encoding each time. I really need a way to do this from the Apple Mail side.
The following is just one example of HTML email I replied and turns out to be BIG-5 under Outlook, but user need to select UTF-8 to view it.
In-Reply-To: <050201c7154d$3fa791c0$bcdd123d@SN012345678912>
References: <[email protected]> <050201c7154d$3fa791c0$bcdd123d@SN012345678912>
Mime-Version: 1.0 (Apple Message framework v752.3)
X-Priority: 3
Content-Type: multipart/alternative;
boundary=Apple-Mail-1--121729776
Message-Id: <[email protected]>
Cc: =?BIG5?B?RXZhSG/EX7XY?= <[email protected]>,
=?BIG5?B?SG9sbHlfUG9sYXLEX7XYs6Ks9cRS?= <[email protected]>,
=?BIG5?B?U3VzYW5hU29vxF+12A==?= <[email protected]>,
=?BIG5?B?UGh5bGxpc8Rftdg=?= <[email protected]>,
=?BIG5?B?S0VOLkpJQbjrvuWoyA==?= <[email protected]>,
"Viv Lee" <[email protected]>,
=?BIG5?B?SmFuZUNoZW6zr6Tlr3U=?= <[email protected]>,
=?BIG5?B?RWR3aW5ZYW+rwKWuxe8=?= <[email protected]>,
=?BIG5?B?MDA3NDalVMBzrvw=?= <[email protected]>
From: James Yao <[email protected]>
Subject: =?BIG5?B?UmU6IMRftdizbqT7pdarfr3osN3DRA==?=
Date: Sat, 2 Dec 2006 07:42:27 +0800
To: =?BIG5?B?vki0ZqzCIEpvYW4gVGFuZw==?= <[email protected]>
--Apple-Mail-1--121729776
Content-Transfer-Encoding: quoted-printable
Content-Type: text/plain;
charset=BIG5;
delsp=yes;
format=flowed
Hi xxxx...... (body of the message)
I need help here, I still like the operation in Apple Mail but this is killing me. Please help.

Thanks but I tried these already. Didn't seem to work.
I switched to Thunderbird. Took a while to convert my mailboxes (30+ of them) from emlx to mbox and loaded into Thunderbird.
Thunderbird is ok, address book really ***** since it doesn't work with the OSX Address book at all. I had to use vcf2ldif to convert address book but the Chinese character in the Address Book all became ??? in Thunderbird. And the time it takes to convert 400+ address is long (I already filtered the address book from my 1000+ contact)
Font setting in Thunderbird is not good as well. Emails in my folders are in different fonts all the time due to the difference in encoding. I just need to get used to it.
If Apple Mail can just handle encoding better, I will never switch. Both my customer and my family are having same problem, (because we all read/send Chinese Traditional email) Apple should do something. Already send email regarding this to Apple, and if there are other people with the same problem as me, pleas let Apple know about this.

Apple mail cannot send

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