a copy has been placed in your outbox. sending the message content to the server failed

Have you checked to see if the server for your email is down or having problems, by doing an email from your computer?

Which type of email is it? Yahoo, gmail, etc.

Confirmed it happens with iCloud mail too, I cannot send emails with attachments from my iPhone. Been happening for months now, have deleted and reinstated my account etc, nothing works.

I'm having the same problem. It's affected my AOL account. I also have 2 other email account and they work fine. I have talked to Aol, AT&T and apple and they all say that the issue is the "other" party. My Aol account works fine on my iPad. MacBook and desk top. In addition to deleting the account, resetting the network connections and the entire phone still no luck. I even entered the account on 2 different iPhones and the same problem happens. I also entered my aol as an other account so I can manually enter all the in/out box settings and still no good. Any other suggestions?

Any ideas on how to solve this? My iPhone is useless if I cannot send email from a 3G connection.

did anyone figure this out? i'm having the same exact issue as described by brandiowen

Yeah, I'm having the same issue with my iphone and ipad. Can receive emails but can't send. Am able to from my laptop.

I think what happened to me was that my yahoo account was compromised by http://thenextweb.com/insider/2013/01/07/yahoo-mail-users-hit-by-widespread-hack ing-xss-exploit-seemingly-to-blame/

Yahoo responds to these reports at the end saying they fixed the issue. I think what that my mobile yahoo mail was somehow blocked by yahoo because that was the device that i logged into right before (the hacker) blasted all of my inbox. That is the only thing I can think of. Exactly 24 hours later I was able to send email. I did figure out that for the iPhone 4gs you can go into your settings and yahoo mail and change the outgoing server from yahoo to gmail if you have gmail set up on your phone and that will allow you to send from yahoo through gmail. I also sent a feedback form to yahoo, that is the only way to contact them, and have heard nothing. There is nothing about this on their support site. So let us know if after 24 hrs you are magically able to send. Yahoo really should use that log in history where they can see that a log in has occurred from a strange IP to block that and warn the user. My log in history right before this happened went: home IP in the US, home IP, homeIP, home IP, Morroco, home IP, home IP, etc. So it is blatantly obvious. My little software company can block IP's, I know yahoo can.

My yahoo is fine, my icloud / me email is f*cked. I rang up Apple and they try to blame my iphone.

I had this problem and resolved it after finding there are not one but two places to enter your email password. The obvious one is in Settings - Mail,Contacts,Calendars - Accounts - (select the account) - Password. I had this one but didn't previously know about the second. Enter the (same) password again in Settings - Mail,Contacts,Calendars - Accounts - (select the account) - Outgoing Mail Server - Primary Server - Password. Maybe an Apple Genius can answer why they require this twice.

I had exactly the same issue with my daughter email address. It took me some time to figure it all out. I did pretty much everything stated above with no luck.

I managed to sort it out in the end by actually sending an email from my daughter inbox directly on hotmail.com. To my surprise Hotmail did ask for a security diagram/code to be entered. Once entered, the email was sent and everything was self sorted and was working as expected.

Bottom line is that the issue was not caused by the IPad but it was Hotmail blocking out the sending of the emails.

Hope it helps!

My issue has been resolved. I did not do anything, it just started to work again one day. I'm surfeit was an AOL issue.

I hope you all get this resolved soon.