one of the recipient addresses is invalid?

Glad to hear! I assumed it was the last step that was needed. I just wrote out everything we tried first. Don't forget to grab iTunes 7.7.1, they'd added a lot of great bugs! Just kidding, honestly haven't downloaded it yet.

I think you guys need to read the thread below.
There are thousands of posts saying they cannot connect to mail servers, cant receive mail without a reboot, cant send mail. Personally I have experienceed all of the above and your problem and dont know what is going on. My opinion after reading all the posts below is that there is an issue with 2.0 and there badly needs to be a 2.01 issued by Apple.

http://discussions.apple.com/message.jspa?messageID=7692335#7692335

First off, check your sent for messages being sent out. Delete it if you can, and the message should stop appearing when you first open Mail.

Next, I'm assuming this started happening after the 2.0 update? This seems to be the case for this issue. I have ran into this twice now and both were after the 2.0 update.

Assuming you updated, try to remember if you had to reenter your email information manually on the iPhone again. If you did not, then it may have been backed up and re-synced to your iPhone automatically. With the current bugs, it'll be best to set up the account manually.

+NOTE: Steps 1-4 may not be necessary. You may try step 5 first and if it doesn't work, perform the entire process.+

The fix I found:

*1. Delete the account on the iPhone.*

Before doing this, be sure you know your settings to recreate this account. If it is one of the prebuilt email addresses (Gmail, AOL, Yahoo, MobileMe, etc), the account settings won't be an issue. If you are using a POP or IMAP account other than the ones built in, contact your email provider for account settings, or, alternatively, look in the Mail Settings on the iPhone before you delete it or online. Some settings include incoming and outgoing server host names, port numbers, whether SSL is used, and authentication type. Don't forget your username and password too!

This may help some of you.
http://www.apple.com/support/iphone/mailhelper/

*2. Once deleted, recreate account*

Enter Settings > Mail, Contacts and Calender > Add Account

*3. Once created, test to see if you receive mail.*

If not and you did before deleting the account, look into your settings, something may have been missed
If it works, continue to the next step.

*4. Check to see if issue still exists.*

Compose a new message AND reply to one

If it works, great. If not continue on.

*5. Enter your Username and Password for your OUTGOING MAIL SERVER*

This is the step that fixed the issue both times when I ran into them.

Go into Settings > Mail, Contacts and Calendar > +Your Account+ > Tap the Outgoing (or SMTP) Server > Tap Primary Server > Enter Your Username and Password in the Optional fields.

Username is usually the first part of your email address (everything before the @) or it can also be your entire email address. Password is the one you'd use to log into its webmail.

Usually, these "optional" fields are truly optional. In this case, having them filled in fixed the issue.

Actually, fixed it twice. Lastly, a hard reset (hold home and power button until screen goes completely off, ignore slide to power off) and a restore are other two options at the end.

Hope this helps you folks.

Good Luck,
Tony

@Digital_Delight,

Unsure what you have tried for Outlook 2007, but here's some quick tips to try (sorted least detrimental to most).

-If your Outlook 2007 has more than one calendar, check them all for the synced information.

-Be sure syncing is set up correctly under the *Info Tab* while your iPhone is connected.

-Reset iPhone (Home and Sleep/Wake button until screen goes off by itself), then try syncing again.

-In iTunes (on Windows), +Reset Sync History+. Which is located under Edit > Preferences > Syncing Tab> Reset Sync History. This does not delete anything of importance. Then try syncing again.

-If you are sure data in Outlook 2007 is more accurate/most up to date you can choose the Replace option at the bottom of the *Info Tab* to replace the data on the iPhone with the data in Outlook.

-Restore iPhone

-Uninstall all of iTunes (no media is lost)

For more help, check these out:
Troubleshooting iPhone and iPod touch contact and calendar syncing via USB on Windows:
http://support.apple.com/kb/HT1692?viewlocale=en_US

Removing iTunes, QuickTime, and other software components for Windows XP:
http://support.apple.com/kb/HT1925 (Vista link located in this article)

Microsoft Outlook 2003/2007 may not display contacts and calendars without refreshing after syncing with MobileMe, iPhone, or iPod touch:
http://support.apple.com/kb/TS1944

Good Luck,
Tony

I'm having the same problem, every mail I try to send gives me the error: one of the recipient addresses is invalid.
And off course he's not sending them.
The addresses I tried are correct and my connection is ok as well, I have the problem both on wifi and in EDGE.
Any thoughts?

Exact same problem here, just started today.

I have my personal doman email as the SMTP server (primary) with my home AT&T, Gmail, and "AT&T SMTP Server" (I assume that is the cell phone one) all activated as secondaries. My primary is also listed as an other server, twice, and neither can be deleted, so I don't know what is going on there.

I have tried turning the phone off and back on, and even a soft reset (power button and home button at same time), and it does not appear to help. Even turned off my primary SMTP and let the secondaries on, still didn't work.

At a total loss here, cannot send emails from my iPhone... HELP!

Thanks,
JoeK

I too have this problem, and nothing seems to work; even after 35 mins on phone to helpdesk.

Please Apple, can you get this sorted; and while you are there can you get Outlook 2007 to sync the calender too. It's a bit disappointing.

James

Hi Tony

Excellent fix thanks. It was entering the username and password in the SMTP Primary SErver area that fixed it for me. I'm delighted to say that all my email accounts are working normally now.

Thanks again.

www.Brian

Thanks Tony for both of your posts.

On the smtpmail front, I still cannot send email. It says that "The connection to the outgoing sever failed.

I have tried a couple of combinations with regards to usernames and passwords, as my ISP stated that I needed to put the entire username in; however, when trying that it stated that it couldn't log in as the username or password was incorrect.

I'll try a reset tonight.

Many thanks

James

Number 5 fixed it for me once I deleted out all the extra outgoing servers, then reentered the correct user name and password. I just spent two hours dealing with this on my bosses phone. Thank you very much Apple!

Tony, thanks! I have Outlook 2007 and was getting an iPhone error (invalid email address) when I would try to reply. Adding my username and password under outgoing/smtp server did the trick!! What a relief!

In case this adds value to anyone... I'm not new to Outlook 2007 and my iPhone never had problems sending out email. The issue started last month when I did two things (don't know which is at the root of the problem) 1) I installed the latest version of iTunes and 2) I launched a MobileMe trial. While I am not tech-savvy, I'm certain that one of these two installs created the problem because the invalid email error began within minutes of installing those two programs. In the meantime, I replaced my original iPhone yesterday with the 3G. The invalid address issue continued until today when I followed your tip on adding username and password.

As a side note, I still seem unable to get out of my MobileMe trial. Account is set to "inactive" but keeps syncing anyway. So, back over to that forum... what else did I have to do this long weekend? 🙂

Erika

GadgetGal08,

The message comes from your outgoing mail server, not Outlook or the iPhone.

One thing that spammers have exploited for over 10 years is mail servers that allow them to send email anonymously. If it is sent anonymously the server takes the blame, not them.

Your outgoing server doesn't want to take the blame so they authenticate who is using them as a relay. There is two ways to do this. The first is to only send for people you are connected to. This is common for Internet Service Providers from dial-up to broadband. If you are at home, connected to their network, such as when you have a router with WiFi and your iPhone connected to that router, username and password isn't required.

The second method is to require a username and password. This is used by a lot of email providers who don't also sell internet connections. GMail, MobileMe, and others are common examples of these.

Some Internet Service Providers (ISPs) also allow you to send with a username and password when you are not connected to them. Some examples include EarthLink, Comcast, AT&T DSL, and others. When they do that they will reject the sender or recipient if their isn't a username and password entered. It may work at home on WiFi, but won't work on cellular data.

Other Internet Service Providers don't offer any option to relay if you are not connected to them. Some examples include Cox, Optonline and Roadrunner. To help in that situations AT&T offers their outgoing mail server that works while connected to cellular data.

If you get an error about one of the recipients or the sender being rejected, first thing to try is putting in username and password for the outgoing or SMTP server. If that doesn't work, try enabling the carrier SMTP server. For AT&T that is cwmx.com for example.

Hope this helps,

Nathan C.

HI there

When I am on the 3G network I can send emails if my mail provider which is my primary server is turned off, but I cannot send emails if my Wi Fi is turned on unless I turn this server back on.With this server back on I cannot send emails via the 3G network!!!! I have tried entering my login and password but this doesn't help either.
Very annoying.

None of these has worked so far for me and I'm on the latest update. It is also random where a couple message during a single day go through just fine then a message to the same account gets flagged and shuts down my iPhone email outgoing.

The iPhone also keeps resetting my settings for the smtp server.

And those who mentioned changing settings on the ATT smtp server, those settings are all gray you can't change them.

I still think it is a bug in the iPhone, this doesn't happen with my iMac or my MacBook on the same account using MacMail.

Message was edited by: Lani Shuck

Same thing here.......