Can't send mail to POP Account which has attachment or signature

Since installing the Update 10.4.6, I have been unable to send email to my pop account which has either a signature or an attachment (when there is no attachment or signature it works fine). I have cleared the caches using tiger cache cleaner. I have tried adding a new user account to mail. It doesn't work in Entourage either. I've reinstalled Mail. What else do you recommend?
Prior to installing the update, mail worked great for over a year!
Additional Information:
Whenever I press the send icon, the mail message disappears, then in the activity viewer it gives the message “Delivering message / Sending data (28% done) and hangs there for a long time and finally gives the following message:
Cannot send message using the server XXX
Use the pop-up menu below to try a different outgoing mail server. All messages will use this server until you quit Mail or change your network settings.
Whenever I send an email with text and a signature, the activity viewer it gives the message “Delivering message / Sending data (100% done) and hangs there for an extremely long time and finally gives the same message.

Mario_MM wrote:
For sending mail the POP server is not important what you need to check are the settings of the SMTP server. Verify the settings of the SMTP server again and compare it to your settings on your iMac.
Checked SMTP settings and they are identical to the working iMac. I had not changed any settings on my MBP when it stopped sending, plus it did work briefly last night with those settings, so I don't see how it could have anything to do with my settings being incorrect.
The only thing even remotely different that I did prior to this happening was to use it away from home. I was out of town and used someone else's wifi to send some emails, but can't see how that should matter. It was the same ISP that I use at home, so I never even had to change settings for remote access. I never touched a thing, but when I got home I could no longer send emails.

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Can't send messages using pop account

Hello,
I can’t send mail with some of my pop accounts using mail app. I have a .mac and a Yahoo account both work perfect. The other POP accounts don’t send. I get an error that says, “Cannot send message using the Server xxxxxxx” I check the setting and they are fine. It stop working a couple of days ago. I didn’t make any changes on the accounts settings.

I had the same problem until I called Earthlink support – it's your ISP's problem not yours. They will help you open a new POP account and set a new port (in the advanced option in preferences) to authorize your ability to send mail. I have no idea whether Yahoo is as helpful as Earthlink. They may not be because they're free.

Can´t send mail on any account

Hi,
Suddenly all of my accounts can´t send mail...
it pops up a window saying mail can´t use this smtp, and it doesn´t matter what I choose for selected server, nothing works.
And if I change the outgoing mail server settings in preferences it does not change in the pop up.
I did not change anything.
I have tried to start new account but nothing works.

Gunz,
For your .mac account, if you are using the smtp.mac.com as the Outgoing Server, change the Port to be Port 587, and test. Although you are using many different venues, more and more ISPs are blocking Port 25 for all but their own SMTP. Are the other accounts unrelated to your ISP? If so, their SMTP may need to be presented either on Port 587, or still another.
If you are having a problem with the SMTP provided by your ISP, then a change in policy may have been accompanied by a new name for their SMTP, or a new Authentication protocol.
More info, please, but first test with Port 587 and the smtp.mac.com.
Ernie

Can't send mail in IMAP accounts after installing Mavericks. Incoming messages OK.

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I'm afraid that I have the very same problem. How did Apple not see this. Surly email is a major part of any opperating system and should have being more than double checked before releasing. I understand software glitches but this is a major pain in the backside. I'm totally stuck and can't use my macbook pro

Z10 Can Receive E-mails from POP Account But Cannot Send/Reply

I am getting seriously frustrated with the inability to send e-mail from this Z10 (bought on 3/28) through my POP account!
I have been able to set up and successfully send through a personal Gmail account but not my "work" POP account. Everything I have read in forums and discussed with my IP and Verizon Wireless points to a bug in the BB10 software. In BB7, even a POP account could be set up very simply and reliably. That was the beauty of BB - simple and reliable e-mail.
I am getting nowhere trying to find a fix or workaround. I reeeeeally wanted to believe that BB was back and that this would be a good phone for me, a BB fan (my third BB btw), but am just a day or two away from giving up and returning the thing. What good is a BlackBerry if you can't send e-mails???? Please help!
BlackBerry Help - what is the fix???!!!! I NEED IT TODAY!!!!!!!
Solved!
Go to Solution.

I have a similar problem. I have three email accounts and two work perfectly (a hosted server and a comcast). However, my Optonline email will not send out attachments or HTML when hitting Reply or Forward. The receiver sees the basic text response and the following (below). Optonline uses port 587 and i think POP, no SSL Optonline, BB and ATT are all looking at it, but no solution yet.
=p style="font-size: =itial; font-family: Calibri, 'Slate Pro', sans-serif; color: rgb(31, 73, 5); text-align: initial; background-color: rgb(255, 255, 255);">Sent from= BlackBerry Z10
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Can't send mail with POP gmail account

Suddenly, when I try to send mail I get this pop-up message:
Enter Password for Account
"smtp.gmail.com:kpellingson"
Please enter the password for user "kpellingson" on SMTP server "smtp.gmail.com"
If I enter my password, I get the same window, over and over.
If I go to gmail's web based mail, my password is accepted and I can send mail, so I know I'm not entering it wrong.
Any ideas?
Thanks,
Karen

OK,
So I'm not crazy.
I agree, I didn't need the "@gmail.com" before. However, when I added it, gmail would accept my password and I could send mail again.
Thinking about this, when I added the "@gmail.com", I had to save the SMTP server settings, hmm..., maybe that old file was corrupted and the new one that I added wasn't... That may be what fixed the problem...just speculation.
Anyway, it's working for me now...Have you tried adding the "@gmail" bit and saving a new SMTP setting? Maybe that will work for you, too.
Good Luck,
Karen
iMacIntel 2Ghz, iMac G3 450MHz Mac OS X (10.4.7)

"Sender Name is Invalid" (can't send email from POP account) iPhone 2.1

I updated from V2.0.2 to V2.1 today. I also swapped out my original iPhone EDGE for a new iPhone EDGE due to unrelated problems with the speaker.
Upon testing things after restoring from backup to the new phone I discovered that I could no longer SEND email from my POP account. I could receive email just fine on that account. Sending and receiving email on my MobilMe account also worked, as did sending and receiving email via the POP account while on the Mac computer I use to sync with this iPhone.
After digging into this with AppleCare we discovered that somehow the Port Address for the Outgoing Mail Server for that POP account had been changed from 25 to 587 on the iPhone.
Changing it back to 25 fixed my problem.
We don't know whether the problem was due to the 2.1 upgrade or due to something in the restore process after swapping the phones.
If you get the error message "Sender Name is Invalid" while trying to send email from a POP account on your iPhone, go to Settings > Mail, Contacts, Calendars and select the line for your POP account.
Now scroll down to the Outgoing Mail Server entry which should show "SMTP" and the name of the outgoing mail server for that POP account. Select that line. This will display a list of servers with your POP account server showing at the top as the Primary Server. Select that line.
In the panel that displays, check the Server Port. If it is something odd like 587, that may be your problem. Select the line and you can edit it to something more normal like 25. Touch the "SMTP" button at the top left of the number entry screen to accept that new value.
We discovered that after correcting that value on the iPhone it STAYS corrected even after doing a new Sync with iTunes, or after MobileMe syncs.
--Bob

Sorry you had problems Bob.
Depending on the mail service you are using, Port 25 or Port 587 are usually acceptable for outgoing
SMTP mail. Many cafes will block the customary port 25 to prevent spammers from using their
wireless access.
There is a superb tutorial posted here:
http://www.webmail.us/docs/support/Macintosh-OSX-Mail.pdf
Also be sure for each mail account to turn ON the secondary AT&T server shown at the bottom
of the SMTP server list for each account -- it will make your transition from wireless to Edge
to 3G networks much more reliable.
Thanks for sharing what you've learned. Hope this helps.

Unable to send Mail from POP account

I have an Iphone 4 and have upgraded the IOS from 5-1 to 6.1.3. Since then I have been receiving all my mails but i have been unable to send mails from my POP account. the notification "Cannot Send Mail. A copy has been placed in your Outbox. The receipient, "xxyyzz @ gmail . com " was rejected by the server" displayed. Please Help. the same thing happens when I configure my POP account on my Son's Iphone4, and there is no problem in receiving and sending mails from my Outlook. Please Help!!!!!
Can i revert back to IOS5.1.1?????

Contact your email provider and get the correct settings to use for the outgoing mail server (SMTP) on a mobile device. If it's email provided by your ISP, they have likely blocked email from outside their network from relaying to prevent spam.

IPod Touch 4 will not send mail (Comcast POP account)

I'm having an issue sending mail (Comcast) in a new iPod Touch. I sync'd it with iTunes and the mail settings are configured exactly as my iPhone (which works sending & receiving). The iPod will receive mail but will not send. It's also able to get online through our wireless network at home.
The only thing I can think of is that it required me to update iTunes to 10.1 (from 10) before it would even be recognized in iTunes. I haven't sync'd my iPhone to the updated iTunes and really am afraid to, if that's what's causing the issue.
Here is the message:
"Canot send Mail"
The connection to the outgoing server "smtp.comcast.net" failed. Additional outgoing mail servers can be configured in settings...."
I can't understand why the iPod's mail settings would be configured any different than the other 4 macs and 1 iPhone in our household.
Any ideas?

Thanks for your help. After further trouble shooting I found that the iPod was conflicting with other outgoing mail servers that were listed as "Other SMTP Servers" in the mail settings. I deleted them and kept only the one that is used for this one email account.
"Authentication" continues to change from "password" to "MD5 Challenge-Response" on it's own. I don't know what that is, so I'll need to check into it to make sure it isn't an issue.

Can't send mail on Comcast accounts

I have turned on servers, entered all info. Correctly. Every time I try to send an email, the message comes back that i have not entered my password. It has been entered numerous times. Same problem on iPad. Any suggestions?

also contacted Comcast. They suggested I download their app for email. Finally looked into Comcast forums and got some info. I did a bunch of stuff so not sure which one helped.. I made sure password was typed into smpt outgoing. From setting tap mail, then tap smpt and there will be a place to put password. Next I took the advice from forum and worked on my email account. I had 12,000 (no kidding) emails in my inbox. I got rid of all spam, unneeded stuff and put all the rest in a temporary folder. That seemed to so do the trick. I can now send emails.
In the Comcast forums there are also screen shots to show you exacly how to configure email for iPhone 5, though it seems the same for iPad, etc.
Hope this helps.

I can't send mail with IMAP account

I have two accounts set up on my iPad, a POP account and and IMAP account. I can send emails on the POP account ok but not from the IMAP account. It is a new email address and I could send emails from it but now it has stopped sending. It says the recipient was rejected by the server or the sender was rejected by the server. No settings have been changed.
Any ideas?
Many Thanks

i think to see al the Sent mailbox present both in the main section both in the imap tree. (see pictures from http://www.pv.infn.it/~bellomo/archivio/Picture%201.png and http://www.pv.infn.it/~bellomo/archivio/Picture%203.png) i've tried to change and use any of the Sent folder as Mail Sent folder from menu, i can change them but trying to send a mail always leave the Sent folder without messages.
Notice that a couple of mails have been copied to Sent folder .... but others not: is so strange !!!
I've tried just after one mail was copied and get the other one not ...

Can't send mail through business account

Hi. I'm using Mail to consolidate various email accounts, and have been having trouble making one of them work.
The connection doctor says it's online and the hosting company for the website says I have the right settings, but it just seems to keep giving me this error message:
And then I have to send it through a different account, which is all sorts of frustrating, as well as debilitating to the business image.
the smtp outgoing setting I was told to use is mail.pepcrealfood.co.uk, which the doctor says is online, as I said. And now I'm being advised to talk to my service provider about it. Any help available out there?

I had the same problem since last Thursday. I have tried and re-tried all of the settings suggested by the support posts but I can not get email to go out of me Outbox.

Help please: can't receive mail on POP account.

Can someone help me? I can't receive emails on my POP account. I am using 10.6.8 os and apple mail 4.6. I'm able to send messages using port 587. Trying to get ready for business launch on Wednesday. Thanks for your help!

Just curious - were you ever able to receive mail or did you recently set this account up and encounter the problem?
As a paying Dreamhost customer, you should have access to their 24/7 tech support. The basic Apple mac.app account set-up is very straight-forward (at least with web mail).
If this is a new account with no received messages, simply deleting it and going through the set-up again is no big deal. Remember, use IMAP instead of POP3 to receive messages. POP3 pulls the only copy of the message off the server and delivers it to your mail client/computer. Since there is no back-up copy of the data on the server, this is bad news if anything happens to it locally.
Here's a basic tutorial on adding/deleting accounts (just in case):
https://www.youtube.com/watch?v=84cYMuVsLp0
Check out this thread as well - appears that even after deleting an account the name of the old account might remain:
https://discussions.apple.com/thread/4094214?start=0&tstart=0
To summarize, I would try the following:
1.) Contact Dreamhost and explain your issue - it could be a problem on their end. Don't be shy about using their tech support; you pay for it!
2.) If Dreamhost finds nothing amiss on their end, you could delete and re-enable your account via mail.app (keeping in mind the caveats about backing-up all received POP3 messages and the potential sender account bug from the thread). Use IMAP if possible.
3.) If that does not work for you, try another Mail client. I recommend Thunderbird, but there are other free options:
http://mac.appstorm.net/roundups/communication-roundup/8-awesome-alternatives-to -mail-app-on-your-mac/
I doubt that this is causing the problem, but you could also disable your firewall (System Preferences > Security & Privacy > Firewall) and see if that changes anything.
Hope one of these works for you.

Can't send mail to .Mac accounts

I saw this problem posted before but the answer didn't solve it for me. I don't have a .Mac account but I use pop mail for my email from my web-based email. Every time I send to a [email protected] address, I get the following message from "Mail Delivery Subsystem" (charles is an example @mac.com address)
The original message was received at Thu, 6 Sep 2007 09:46:33 -0700 (PDT)
from smtpout09-04.prod.mesa1.secureserver.net [64.202.165.17]
----- The following addresses had permanent fatal errors -----
<[email protected]>
(reason: 550 5.1.1 unknown or illegal alias: [email protected])
(expanded from: <[email protected]>)
----- Transcript of session follows -----
... while talking to smtp-bounce.mac.com.:
DATA
<<< 550 5.1.1 unknown or illegal alias: [email protected]
550 5.1.1 <[email protected]>... User unknown
<<< 554 5.5.0 No recipients have been specified.
Reporting-MTA: dns; mac.com
Received-From-MTA: DNS; smtpout09-04.prod.mesa1.secureserver.net
Arrival-Date: Thu, 6 Sep 2007 09:46:33 -0700 (PDT)
Final-Recipient: RFC822; [email protected]
Action: failed
Status: 5.1.1
Remote-MTA: DNS; smtp-bounce.mac.com
Diagnostic-Code: SMTP; 550 5.1.1 unknown or illegal alias: [email protected]
Last-Attempt-Date: Thu, 6 Sep 2007 09:46:35 -0700 (PDT)

This is only a guess, as there is no host "smtp-bounce.mac.com": your mailserver smtpout09-04.prod.mesa1.secureserver.net is currently listed at least at one blacklist service (take a look here http://tqmcube.com/cgi-bin/rbltqm?ip=64.202.165.17 to verify) as a spammer.
I am not sure about the technology Apple uses to prevent SPAM, but it technically would be possible to check for listed servers before establishing a connection and saying "HELO" with a faked hostname (smtp-bounce.mac.com in that case) and bouncing all mail.
The second possibility is, of course, that the given error "User unknown" is correct, and the user imply does not exist.
Try figuring this out by sending mail to .Mac users using an alternative mail provider or SMTP-server.

Brand new macbook pro can't send mail through verizon account

Hi,
I just bought a 13 inch macbook pro, 750 gb hard drive I7 processor. I can receive mail, but can't send it through my verizon account. My mobile me account works fine. Everything looks right but it just won't send. Any ideas?
thanks,
Joe

I had the same problem since last Thursday. I have tried and re-tried all of the settings suggested by the support posts but I can not get email to go out of me Outbox.

Can't send mail to POP Account which has attachment or signature

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