How To Fix Palm Pre's "Error Sending Mail" Problem
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The Problem
My fiancée Emilie has had her Palm Pre for about 2 weeks now, and one specific problem that started showing up last week has been incredibly annoying, causing us all kinds of trouble.
After Emilie got the phone, she added 3 email accounts – Gmail, Hotmail, and Yahoo. One day, after sending an email through the Pre, a popup showed up that said "Error sending" followed by the subject of that specific email. Swiping the error away didn't help – it just came back 5 minutes later. In fact, it has been coming back every 5 minutes of every day since, lighting up the screen each time. Thus, not only it was annoying, but it was running down the battery like crazy – a full charge lasted between 1/2 and 3/4 of the day with very mild usage.
I deleted the problematic message from the Outbox a long time ago. The error didn't disappear and kept popping up. Additionally, whichever Outbox clicking on the annoying popup led to was having trouble refreshing, even though it wouldn't display what the error actually was – just a yellow exclamation sign would show up. Refreshing the folder didn't help and would take an unusually long time.
Well, finally, I got sick of waiting for Palm to update its OS with possible fixes and set out to find one myself.
Turns out a ton of people are having the same issue, as evident in all Palm Pre forums. For example, Palm.com forum or Precentral.net forum. I really didn't like the common suggestion to delete and re-add the problematic account because
- that just most likely temporarily pushes the problem back as I'm sure it would come back again to haunt me
- this could potentially erase or disconnect all contacts associated with that account
- my engineering mind would be left puzzled
- I wasn't sure which account was having the problem (later it turned out the culprit was Yahoo)
Surprisingly, I found the clue that led me to the solution on Yahoo Answers – yeah, that place where nothing intelligent is allowed to exist (with certain exceptions).
The Solution
To make a long story short, Pre messed up Yahoo's outgoing mail settings. My particular problem was the SMTP (that's the outgoing mail server) port was set to 995, which is in fact an incoming POP3 mail server port. I don't know how it happened or if it even worked in the first place but the fact is: the right outgoing port for secure (SSL) SMTP connections is 465. Also, for some reason the SMTP username was blank but the password was filled in. WTF, Pre?
When I changed SMTP port to 465 and entered the username, as specified in that Yahoo Answers post (without the @yahoo.com part), the error message went away and the Outbox refreshed just fine. BTW, my Pre has the incoming mail server set to POP3, while the Yahoo Answers post was set to IMAP – again, why the differences? I'd frankly prefer IMAP anyway.
To get to your mail account settings, open up your email application, go to the Email menu in Pre's top left corner, tap Preferences & Accounts, then tap the offending account, scroll down, and tap Change Login Settings. When you are done, just swipe back (half swipe from right to left in the gesture area). Here's a handy screenshot I took of the relevant area:
-> 
In the meantime, here's a handy excerpt with port numbers for various connection and server types:
- POP3 – port 110
- IMAP – port 143
- SMTP – port 25
- HTTP – port 80
- Secure SMTP (SSMTP) – port 465
- Secure IMAP (IMAP4-SSL) – port 585
- IMAP4 over SSL (IMAPS) – port 993
- Secure POP3 (SSL-POP) – port 995
If you are experiencing the same symptoms, check ALL your mail settings, not just the ones I mentioned. Who knows what else your Pre may have messed up?
Update: if you are having trouble sending your mail while on WiFi only, it is possible that your router is blocking the needed ports. Try to edit the router configuration and open the ports used by your Pre's mail configuration – hopefully the problem will be solved.
Conclusion
Palm, are you hearing us? We are not happy with the bugs and the unhelpful error messages (or lack thereof altogether)! 3 measly updates in the last 2 months is quite pathetic. I hope you are working on a much bigger update behind the scenes.
Artem Russakovskii is a San Francisco programmer, blogger, and future millionaire (that last part is in the works). Follow Artem on Twitter (@ArtemR) or subscribe to the RSS feed.
In the meantime, if you found this article useful, feel free to buy me a cup of coffee below.
beer planet is a blog about technology, programming, computers, and geek life. It is run by Artem Russakovskii - a local San Francisco geek who currently works at 
Artem loves commenting on other people's blogs and reading comments on his own, so go ahead and leave one.
Emillie should remove the account, re-add the account and restart the device: launcher>device info>scroll to bottom to, reset options> restart. Its the first icon for restart.(green).
I ended up back on my blackberry curve waiting for the Tour.
For what it's worth, I added my Yahoo account to the Pre, and it didn't have either of these problems — incoming mail is IMAP (not POP3) on 995, outgoing is myusername@yahoo.com with a password set on port 465 of palm.smtp.mail.yahoo.com.
I do see a different and annoying problem with the Yahoo account where, even though the credentials on the phone are correct and work most of the time, sometimes they stop working for a few hours (during which time I get a bunch of "authentication failed, click here to enter the right credentials" messages), and then it starts working again without me changing anything. http://forums.palm.com/palm/board/message?board.id=wireless_email&thread.id=8764 for that one.
@Matt
That's the mind boggling part – when I added the Yahoo account on the emulator, everything was fine.
I even think that when I just added the Yahoo account that very first time, it was also fine. But then something triggered it to erase part of its information.
Many people are having this problem and I don't know why.
That is exactly what happened to my wife's pre. The gmail outgoing port was 993 rather than 465. Made the change and the problem was gone. Thanks.
This is great! Fixed the error my wife was getting on her Pre. Not sure why Gmail wasn't setup to use SSL encryption or why the port was wrong when I turned it on. But your tip finally led me to the fix that worked!!! Thank you!
No probs, guys. This had to be shared, as it was such a huge pain in the ass. Glad it helped.
much appreciated solution. so far so good. finally sent a couple of emails sitting in my outbox for a couple of days. & hopefully the "login rejected" msg from Yahoo will stop showing.
After being in the Sprint store for 3 hours, on the phone with Palm, on the phone with Sprint…..searching the Internet for fixing this outgoing email problem I find this blog. This is the best answer and complete after all the searching, phone calls and in person waiting. Hats off to Mr. Beer Planet. UNFORTUNATELY I followed this to a tee with no results. I've tried everything and ready to throw it in. I guess I'll get a belt clip for my laptop so I can just carry that around everywhere I go. My case must be "special". Good blog however.
Trick
@Trick
As I've learned, with this phone, even the most logical things become illogical and broken for no reason. I hope you sort it out in the end.
Have you upgraded the WebOS to at least 1.1? It may help fix some of these things.
Yo, Mr. Beer. I am current with WebOS and will have to just wait for the fix. I think this is a palm OS issue as the rest of the phone works great. No complaints. After my exhuasting web search there are lots of people with this problem and basically it appears to be a hit and miss thing, which of course, I seemed to have fallen in the "hit column. I haven't shot my 12 guage in a while. If I get too annoyed it get inroduced to skeet and some phesant shot. fyi, fwiw, I have friends here in Des Moines from both Ukraine and St. Petes.:) Thanks for the reply. If I find an answer I'll come back and post. Thanks
Trick
I LOVE YOU! Thank you so much – this issue was driving me insane. And, I was getting very sick of my husband and friends saying 'See, you should have just bought an iPhone."
I'm not technical at all, but was able to follow your simple instructions and it worked. (Changed the port to 465 from 993).
Now, if Palm would fix this in addition to (1) augmenting the woefully inadequate battery (2) add voice dialing and (3) visual voicemai – we'd be all good!
Thanks Again
This fixed the problem sending new mail, but I still can't send mail when I try the reply button.
Hello anyone, I have tried the couple of things since I first posted but sending out email, whether new or reply, still doesn't work. I find it amazing that some work and some, like me doesn't. For outgoing should we be using authentication? Any more ideas?
Thanks.
Trick
i can not send messages plese help me
I just got my Pre on 9/14/2009 and I have Palm webOS 1.1.0
I just had the same issue. I couldn't send. Tried SSL, nope. I have a Gmail account and tried that fix, nothing. So I deleted both POP accounts and added them again.
Bingo!
I can send mail now.
Doesn't make any sense, but my pop email works now.
Hope this helps someone else.
Kelly
This didn't fix it for me, please respond.
Any suggestions on how to fix the problem if you have an earthlink account? THANKS!
Hello everyone, just thought i would pass along that i finally did get it to work. it took about 4 trys of deleting the account and re making the account. I did finally get it!!! thanks for all the help.
jpt
I have the same problem, but with my work email. all the settings are correct because I compared my settings from Outlook (which is working fine) to that of my PRE [which is recieving an error message of Email App Alert].
Please help. I have 2 different email accounts on my PRE, GMAIL which works fine, and my work email which WILL NOT work!!! please HELP! even the PRE rep could not help me
I had to do a work around – my work email comes in fine, but will not send, so I use gmail when I respond. Just have to remember to switch accounts before sending
That cant be the only solution, because before I did a master reset on my pre, all my accounts were working fine, gmail & work mail.
Mine worked fine in the Sprint store. Have not tried deleted and re-adding my work email with WI-FI off yet.This works for some.
Thanks for this article! Got my mail to sync properly FINALLY.
[...] I just figured out the problem before finding this and my results are similar to jamiespeck's findings. I made a post about the solution with some illustrations that Pre users will hopefully find helpful and perhaps Palm will notice and fix the problem. The post is here: How To Fix Palm Pre's "Error Sending Mail" Problem | beer planet [...]
[...] I didn't like the "delete and re-enter your email information" solution at all and I believe I found a proper solution to the "Error sending mail" problem and made a post about it with some illustrations that Pre users will hopefully find helpful and perhaps Palm will notice and fix the problem. The post is here: How To Fix Palm Pre's "Error Sending Mail" Problem | beer planet [...]
[...] Read the original post: How To Fix Palm Pre's "Error Sending Mail" Problem | beer planet [...]
[...] I never heard back from him. I tried all the fixes listed in these comments and from the page How To Fix Palm Pre's "Error Sending Mail" Problem and none worked. When I read about the NAI that is something I hadn't checked and b/c I was using [...]