Mails sent on my iPhone isn't shown in the sent folder

Whenever I send an email it does not show up in the sent folder on my iPhone or on my Mac when I sync. Why could this be?

It works just fine, I recieve mails and I'm able to reply and all that. I just can't see them in the sent folder which is annoying.

Hope you can help me 🙂

MacBook, Mac OS X (10.5.1), 2.0 GHz - 2GB RAM - 80GB HD

Posted on Aug 4, 2008 5:13 PM

Top-ranking reply

Markus Hänchen

Level 1

140 points

Posted on Aug 22, 2008 12:34 PM

I think figured it out. The original problem was that Mail.app was not using Gmail's smtp server. In the account preferences in Mail I have checked the box which says: 'Only use this server' under the pop-up list which has Gmail's smtp server selected. But examining the full headers of emails sent via supposedly different smtp servers (via different email addresses with all have that 'Only use this server' checked) and emails sent via Gmail's web interface gave me the strong indication that Mail.app is not using Google's smtp server.

Lo and behold, once I switched between my corporate network and a cellular-modem based one which caused Mail to fail to reach the smtp server (inside my corporate network only my corporate smtp server works and outside every smtp server except the corporate one works) and therefore brought up a dialogue which allowed me to choose the smtp server and I selected Gmail's smtp server, my sent messages showed up in Gmail's sent folder.

Even better, after restoring my iPhone (syncing wasn't doing the trick), emails sent from my Gmail account on the iPhone show up in Gmail's sent folder (and Gmail's sent folder also shows up on the iPhone).

As usual, if you for your life's sake cannot figure something out, most likely something you consider a fact is actually not the true. I was assuming that Mail was using Gmail's smtp server, that is what I told Mail to do. But apparently, once Mail fails to reach an smtp server and you tell Mail to use another it continues to use this alternative server forever until it fails to reach this one and ask you again (and that is the only way to reset it). And more importantly this alternative smtp server gets carried over to the iPhone. Even more sneakily, if you check the smtp server setting on the iPhone it still reads the 'correct' one but it is using in fact another one (visible from the full headers of the received email).

Getting Mail to use the correct smtp servers is its own pain in the butt. And after the umpteenth restore with everything working now, I now unchecked the option to sync mail accounts (since I keep switching networks on my Mac, I'm sure to end up with the wrong smtp servers associated with my email accounts).

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40 replies

Aug 26, 2008 2:36 AM in response to Markus Hänchen

They don't look the same. If I send an email to myself from the Mail.app the "Recieved" part look like this:

from ?192.168.0.8? ( [85.81.184.74]) by mx.google.com with ESMTPS id 3sm6467842eyi.5.2008.08.26.02.27.06 (version=TLSv1/SSLv3 cipher=RC4-MD5); Tue, 26 Aug 2008 02:27:07 -0700 (PDT)

If send from my iPhone to myself it looks like this:

from ?192.168.0.2? ( [85.81.184.74]) by mx.google.com with ESMTPS id 5sm6366551eyf.8.2008.08.26.02.28.05 (version=TLSv1/SSLv3 cipher=RC4-MD5); Tue, 26 Aug 2008 02:28:06 -0700 (PDT)

Why could that be you think?

Actually emails sent from my iPhone do show up in Gmail accessed through Safari! Very strange... I never thought about checking that.

Aug 26, 2008 2:57 AM in response to Rune Neesgaard

The good news is you are sending via the correct smtp server when sending from the iPhone and the (sent) emails get stored on the server in the Sent folder (the two 'Received' entries both indicate that the email was sent through Google's smtp server, a different originating IP is to be expected since the two emails were sent from different devices).

Now something very funny seems to be happening, since when you send an email via the web interface it gets stored in the online Sent folder, you can see the contents of this online Sent folder via the iPhone but when you send an email via the iPhone it also gets stored in the online Sent folder but does not show in Sent folder accessed via the iPhone. Either something is not really what it appears to be, or Gmail is tagging emails sent from the iPhone differently than those sent online via the browser.

Aug 26, 2008 3:39 AM in response to Markus Hänchen

"Now something very funny seems to be happening, since when you send an email via the web interface it gets stored in the online Sent folder, you can see the contents of this online Sent folder via the iPhone but when you send an email via the iPhone it also gets stored in the online Sent folder but does not show in Sent folder accessed via the iPhone. Either something is not really what it appears to be, or Gmail is tagging emails sent from the iPhone differently than those sent online via the browser."

That's not quite right. It's very confusing, but I'll try and make it more clear:

Emails sent from Mail appears in the iPhone's sent folder and the web interface's sent folder.

Emails sent from the web interface doesn't appear anywhere - not in Mail.app's sent folder or in iPhone's sent folder.

Emails sent from the iPhone appears in the web interface's sent folder, but not in the Mail.app's sent folder.

It's getting hard to keep track of, but I think this is about right 🙂

Sekoya

Level 2

265 points

Aug 26, 2008 5:06 AM in response to Rune Neesgaard

Emails sent from Mail appears in the iPhone's sent folder and the web interface's sent folder.

Emails sent from the web interface doesn't appear anywhere - not in Mail.app's sent folder or in iPhone's sent folder.

I think that is where the problem is there is no synchronisation between the Sent folder on the server and your local one (eg, the one in Mail.app). Since you use the Google's SMTP server (and authenticate with your email address), sent emails get stored on the server but the two Sent folders (server and local) are not synchronized at all. Emails sent from Mail.app get stored locally and on the server but not because the folders are synchronized but because Mail.app adds it to the local Sent folder and the SMTP server adds it to the online folder.

Emails sent from the iPhone appears in the web interface's sent folder, but not in the Mail.app's sent folder.

I just read through your posts again, do you see anything in the Sent folder on the iPhone (emails sent from Mail.app or the web interface)?

Here are screenshots of my settings in Mail for my Gmail account.
http://img398.imageshack.us/img398/9772/gmailsettingsgb5.png
I'd think if you get the Sent folders (online and local on your Mac) synchronized, a restore of iPhone should get it working there as well. What might be still missing is this step:
In Mail's sidebar you should have a category called GMAIL (or the like), if you open all disclosure triangles there should be a Sent folder. Highlight that Sent folder (click on it), then go to the menubar: 'Mailbox' -> 'Use This Mailbox For' -> 'Sent'
You now should have a subfolder 'GMAIL' in your Sent folder in Mail.app:
http://img205.imageshack.us/my.php?image=sidebarka2.png

Don't get confused by my split personality.

Aug 26, 2008 6:14 AM in response to Sekoya

"I just read through your posts again, do you see anything in the Sent folder on the iPhone (emails sent from Mail.app or the web interface)?"

Yes, I see emails sent from the Mail.app, not from the web interface.

Almost all of my settings were like yours, but not all of them. I changed those that weren't so I now have the exact same settings as you (except for the Trash and Junk ones, I don't suppose those'll matter that much).

"In Mail's sidebar you should have a category called GMAIL."

I remember having had a such, but it's not there anymore for some reason. Do you think that is where the problem is and the reason why my web interface and Mail.app doesn't sync? If so, do you know how I can fix this?

"Don't get confused by my split personality."

I'll try hard not to 😉

Sekoya

Level 2

265 points

Aug 26, 2008 6:44 AM in response to Rune Neesgaard

Whenever you set up a new IMAP account, Mail.app will download the list of folders already on the server and create that category in the sidebar. It will automatically create a unified inbox (ie, the inbox found on the server will be made a subfolder of the local inbox). Other folders like Sent, Trash etc. might be unified (but certainly won't if there is a name mismatch, eg, if the folders on the server are labelled in a different language). By using that 'Use This Mailbox For' command you can force that 'unification'.

I think it is quite likely that the missing synchronisation and the missing GMAIL category are linked. Now, how to get that back, I don't know. In my case, I even went so far as to remove the Gmail account completely from Mail and added it again (just wanted to make sure I followed Google's instructions). All mail in your inbox should not be affected by this as it remains on the server and can be downloaded again (manual filing in contrast to rule-based filing would have to be re-done). I took the precaution of copying all locally stored sent messages in a temp folder (in Mail).

Aug 26, 2008 6:55 AM in response to Sekoya

I don't know why, but after changing the settings so they matched yours, Mail started downloading and now I have two folders called Gmail (the first one [Gmail] and the second one just Gmail).

In the first are the following folders (I don't know if I get all the names right, I'm translating them from danish and I'm not sure what they're called in english, but you can probably figure it out): All Messages, Drafts, Deleted Messages, Sent Messages, Junk and (Star) Marked.

In the second one are: Apple Mail To Do, Deleted Messages, Drafts and Sent Messages.

Should I now tell each of the two folders called Sent Messages to "Use This Mailbox For" -> "Sent" and restore my iPhone??

Aug 26, 2008 7:18 AM in response to Sekoya

I tried removing my IMAP account from Mail and making a new one following the instructions from Google. I get the same result: Two Gmail folders containing the folders that I mentioned before. But selecting "Use This Mailbox For" -> "Sent" doesn't move the Sent folder up to the normal Sent folder in Mail like it did in your screenshot. In the Trash folder (Mail's Trash folder, the one with the icon) I can click a triangle and I see two Trash folders: One called "On My Mac" and the other one called "Gmail". I suppose that's how the Mail's Sent folder should like like two, right?

Aug 26, 2008 7:59 AM in response to Sekoya

I just tried that. It sets up the account in the same way. With two Gmail folders. And actually, I think I left that out before, there are 3 Sent Messages folders besides Mail's standard Sent folder with the icon! In the first Gmail folder are, among the others I mentioned earlier, one called "Sent Messages" and one called "Sendte e-mails" (which is just Sent Messages in danish). And then there are the other Gmail folder where there is one called "Sent Messages".

You wouldn't think it was supposed to be this messy. Any ideas about what to do?

Thank you for your help so far!

Sekoya

Level 2

265 points

Aug 26, 2008 8:19 AM in response to Rune Neesgaard

At least your messiness is reproducible ::). I had the same problem of having both a German and an English Sent folder with another IMAP account (non-Gmail). I 'solved' the problem by logging into the server hosting my IMAP account and changing my language there to English (my local system is also English) and deleting any remaining German (duplicate) folders in Mail.

In the first Gmail folder are, among the others I mentioned earlier, one called "Sent Messages" and one called "Sendte e-mails" (which is just Sent Messages in danish). And then there are the other Gmail folder where there is one called "Sent Messages".

Try sending emails from the web interface and see whether they show up in any of local Sent folders (after a check Mail in Mail.app). If they show up in one of the folders, select this one and use 'Use This Mailbox For' command on it. Then delete all other local ones (if they get recreated, check in the web interface whether you have multiple Sent folders there as well).

Sekoya

Level 2

265 points

Aug 26, 2008 9:18 AM in response to Rune Neesgaard

In the second one are: Apple Mail To Do, Deleted Messages, Drafts and Sent Messages.

I just checked in my Gmail account, these names correspond to labels that are created in the web interface to reflect local folders. But the 'Apple Mail To Do' folder is on my system a subfolder of the iconized (local) To Do folder. In your case the labels in Gmail however then triggered new local folders instead of integrating with the existing ones of the same name. Not having everything in English might be a reason triggering this mayhem.

Aug 26, 2008 9:20 AM in response to Sekoya

I removed the account once more, changed language in my web interface and created it again. I still have 3 sent folders, but I don't think that matters that much. I located the one syncing with the web interface and did the "Use This Mailbox For"-command on it like you said and Mail.app moved that folder to Mail's Sent folder. It seemed to be working so I deleted the other two Sent Messages folders, but when I then looked in the Mail.app on my iPhone where was no Sent folder at all!

Aug 26, 2008 9:22 AM in response to Sekoya

"Not having everything in English might be a reason triggering this mayhem".

That's strange because I have everything in english. I changed my web interface to english and my Mac is always set to english.

Sekoya

Level 2

265 points

Aug 26, 2008 9:31 AM in response to Rune Neesgaard

If you are sure that the synching between the Gmail server and Mail.app works (ie, writing an email on either interface causes it to show up in to other Sent folder as well), I would attempt another iPhone restore.

Aug 26, 2008 10:12 AM in response to Sekoya

Okay, now it seems to be working. A few more problems though:

1. Now all the Gmail folders shown in Mail.app is showing in my iPhone Mail to. Can I do anything about that?

2. New mail is shown both in my Inbox in Mail.app and in the Gmail folder in Mail.app and it looks like the batch that displays the "New Mail count" is not going to go away unless I click in the new mail on both my Inbox and the Gmail folder. Does that sound right?

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Mails sent on my iPhone isn't shown in the sent folder