Achieving Email Bliss with IMAP, Gmail, and Apple Mail

On 15-May-2009, at 02:30, B12 Partners wrote:
> No way IMAP would work for this, we are already stressed enough.


Oh no, IMAP works just fine with this. It is Gmail that seems to
create multiple copies of the drafts. Or maybe it is Mail.app w/
gmail? I have to go through every month or so and delete old drafts,
and almost all of them are in the gmail drafts folder.

Matt Neuburg wrote:
> The *real* problem comes when it's time to send the message. Gmail won't
> send it until it has saved a draft, so the entire attachment must be
> uploaded a minimum of twice. In my actual usage, where I sometimes write
> and rewite even those "couple of lines", it often happens many more times
> than that.

To be clear, this only occurs when using a third-party Mail client
with Gmail, right? The Gmail web app only seems to store attachments
once, and sending attachments to the server seems to have nothing to
do with saving drafts at all; the two actions occur independently of
each other.

Using the Gmail web app, the attachment is sent to the server as soon
as you attach it (whether or not you save the mail's draft), and is
not sent again unless you remove it and attach it again - at least as
far as I can tell.

Lukas

--On May 15, 2009 1:30:15 AM -0700 B12 Partners <sethb12partners.net>
wrote:
> This information gets saved to our network, and re-sent elsewhere.
> Sometimes we'll work on an email for 3 days before it gets sent: changing
> attachments, updating attachments, replacing attachments, revising the
> email text as information changes. No way IMAP would work for this, we
> are already stressed enough. --

Others have pointed out this isn't a requirement of IMAP, it's more the way
the client side works. It's actually a way of saving your messages if your
local machine, or e-mail client crashes. It's auto-saving your message.
Microsoft Exchange supports this mode of working as well. Using Outlook it
auto-saves messages every few minutes.

It is annoying with a GMail implementation because it's slow across the
internet to do the autosave. With my own local IMAP server, or at work with
a fast connection to the server, it's very nice feature. I can start an
e-mail, leave, open up the auto-saved draft from another e-mail client
(i.e. my iPod Touch or my web mail client) and finish the message.

My IMAP client, Mulberry, has an option to save Drafts locally or to the
server, and how frequently it occurs. Outlook can be configured how
frequently it saves to the server (I think the default is 15 minutes.)

Kevin

--On May 15, 2009 1:30:15 AM -0700 David Ross <drdavidrossconsultant.com>
wrote:

> If your email is business based and that business requires trading files
> such as CAD, scans, etc... then attachments over 1MB are a way of life.
> In these cases I can't see switching from in house mail servers to GMail.

As a system administrator for a document management system dedicated to
engineering projects, including many, many CADD files, I have to say
e-mail, any e-mail, is absolutely the worst way to manage files. But even
so we've had to increase our limit on attachment size to accommodate larger
files (or more files bundled as zips) being sent over e-mail. I think
we're allow 20-40mb attachments now.

--On May 15, 2009 1:30:15 AM -0700 Matt Neuburg <matttidbits.com> wrote:

> The draft upload occurs very often - so often that while you pause to
> consider those couple of lines, it has started.

This can be disabled on a per account basis in Mail.app. Under "Mailbox
Behaviors" for the account just uncheck "Save draft messages on the server"

Kevin

I had the same problem and tried several "tricks" with no luck. In the end, I fixed it by deleting the account from Mail and adding it back.

-Theo

On 17-May-2009, at 05:23, Kevin van Haaren wrote:
> --On May 15, 2009 1:30:15 AM -0700 David Ross <drdavidrossconsultant.com
> >
> wrote:
>> If your email is business based and that business requires trading
>> files
>> such as CAD, scans, etc... then attachments over 1MB are a way of
>> life.
>> In these cases I can't see switching from in house mail servers to
>> GMail.
>
> As a system administrator for a document management system dedicated
> to
> engineering projects, including many, many CADD files, I have to say
> e-mail, any e-mail, is absolutely the worst way to manage files.
> But even
> so we've had to increase our limit on attachment size to accommodate
> larger
> files (or more files bundled as zips) being sent over e-mail. I think
> we're allow 20-40mb attachments now.

With the rise of simple to use services like Dropbox and others I have
gone the other way and reduced my max message size down to 10MB from
the 15-20MB it's been since around 2001.

I get a complaint every now and again and I simply point them to their
webdav accessible storage or to services like Dropbox that are simple
enough for "Mom" to use.

My mailserver is a lot happier too.

OTOH, my sister tried to email a 330MB movie file which somehow ened
up being saved in her drafts folder. (Max message size in Postfix
doesn't come into affect until you try to send the message).

Kevin van Haaren wrote:
> --On May 15, 2009 1:30:15 AM -0700 David Ross <drdavidrossconsultant.com>
> wrote:
>
>> If your email is business based and that business requires trading files
>> such as CAD, scans, etc... then attachments over 1MB are a way of life.
>> In these cases I can't see switching from in house mail servers to GMail.
>
> As a system administrator for a document management system dedicated to
> engineering projects, including many, many CADD files, I have to say
> e-mail, any e-mail, is absolutely the worst way to manage files. But even
> so we've had to increase our limit on attachment size to accommodate larger
> files (or more files bundled as zips) being sent over e-mail. I think
> we're allow 20-40mb attachments now.

I was implying trading files, not managing them. But I don't like it either. But architects and engineers have adopted email as a way to trade files. It's a fact of life. So we deal with it. And yes we also have an FTP site but again, email with large attachments is a reality.

David

--On May 17, 2009 1:48:49 PM -0700 David Ross <drdavidrossconsultant.com>
wrote:

> Kevin van Haaren wrote:
>> As a system administrator for a document management system dedicated to
>> engineering projects, including many, many CADD files, I have to say
>> e-mail, any e-mail, is absolutely the worst way to manage files.
>
> I was implying trading files, not managing them. But I don't like it
> either. But architects and engineers have adopted email as a way to trade
> files. It's a fact of life. So we deal with it. And yes we also have an
> FTP site but again, email with large attachments is a reality.

We found too many mistakes when using this method (always a question of who
has the most up-to-date file and who has the correct file, not always the
same person) so our document management system completely replaces file
transfer altogether. External and internal users work from the same file
set and the software manages the back end so people are working from local
up to date copies. It's far from perfect but has reduced file transfer
nightmares on projects using it significantly.

File transfers are still needed (usually more of a one time thing, not for
in use files) but we no longer have an FTP site for any file transfer (this
pre-dates the system above) because security was too hard to maintain on
it. We use a system similar to .Mac/dropbox/box.net systems where you
e-mail a link, ours is secured by generating passwords for users that need
to pick up files.

I recently switched to IMAP (gmail, Mail.app, and iPhone) and have run into a problem I don't believe anyone has mentioned in this regard: if you read mail on your iPhone or google's web interface, when the messages are downloaded to your computer (assuming you are keeping copies there), Mail.app's rules will not be applied. Apparently Mail.app only applies rules to "unread" mail. Is that correct?

On 19-May-2009, at 01:54, pmcclure wrote:
> Apparently Mail.app only applies rules to "unread" mail. Is that
> correct?

I've done some testing with mail.app rules and have found them to be
very ... um... crappy.

The last one I tried simply did not work:

If [all] of the following are met:
    From is "kremekreme.com"
      To is mymac.com.email
Subject is AUTOREPLY

perform the following actions:
   [Reply to Message] (Reply message text)

message comes in matching the conditions and -nothing happens-

On 2009-05-20, at 09:40, LuKreme wrote:

> I've done some testing with mail.app rules and have found them to be
> very ... um... crappy.
>
> The last one I tried simply did not work:
>
> If [all] of the following are met:
> From is "kremekreme.com"
> To is mymac.com.email
> Subject is AUTOREPLY
>
> perform the following actions:
> [Reply to Message] (Reply message text)
>
> message comes in matching the conditions and -nothing happens-

1. One person's inability to get rules working doesn't make Mail's
rule handling crappy

2. Try 'contains' instead of 'is'. I think Mail checks both the name
and address (i.e. full string after 'From:' in raw message)

On 20-May-2009, at 00:33, Tom Robinson wrote:
> 1. One person's inability to get rules working doesn't make Mail's
> rule handling crappy

True, but that is certainly not my only experience with the crappiness
of Mail.app's rules.

> 2. Try 'contains' instead of 'is'. I think Mail checks both the name
> and address (i.e. full string after 'From:' in raw message)

Oh, I tried many variations, none worked. And, in the interest of
full disclosure I was only doing it to confirm someone else's
experiences with the reply to message not working on their machine or
on the friend's machine they were trying to solve the problem on.

I've always found Mail.apps rules to be weak, have extremely limiting
actions, and have seen then fail for no apparent reason on many
different people's machines. The usual scenario is "This rule has been
working for 3 [months|years]. This morning it stopped working" at
which point the only solution seems to be delete the rule and remake
it. And cross your fingers.

I don't actually use them myself, I use procmail.

Good article thanks.

Just wondering, you set up IMAP like this, and have the IDLE preference selected in Preferences --> Accounts --> Advanced, then what function does the "Get All New Mail" command have in Apple Mail?

a.k.a. the Get Mail button in the toolbar. I know clicking on it causes lots of activity in my Activity Window. But is clicking this button just a bad habit from the POP days, and can I get rid of that button?

Thanks.

fcchuan wrote:

Just wondering, you set up IMAP like this, and have the IDLE preference selected in Preferences --> Accounts --> Advanced, then what function does the "Get All New Mail" command have in Apple Mail?

It checks your mail, just like always! (And does so for all accounts, by the way.)

For me at least, IMAP IDLE has never worked with Gmail and Mail. For example, if I enable IDLE support in Mail and set mail checking frequency to Every Hour, or Manually, and then go to another client and send myself messages, they don't arrive. If I check manually, or turn the schedule back on/up, they do. I've tested this quite a few times under numerous different conditions, and I always get the same result. So, I don't know if it's Gmail, or Mail, or something in between that's broken, but the only thing that has worked for me is automatic checking manually or on a schedule.

a.k.a. the Get Mail button in the toolbar. I know clicking on it causes lots of activity in my Activity Window. But is clicking this button just a bad habit from the POP days, and can I get rid of that button?

If you set Mail to check automatically (anywhere from every minute to every hour), then you don't need to click that button. And if for some reason the button just really bothers you on the toolbar, you can remove it and use Command-Shift-N to check for new mail if needed.

Joe

On May 21, 2009, at 8:56 AM, fcchuan wrote:

> a.k.a. the Get Mail button in the toolbar. I know clicking on it
> causes lots of activity in my Activity Window. But is clicking this
> button just a bad habit from the POP days, and can I get rid of that
> button?


Easy squeezy. Simply right-click anywhere in the button bar, choose
"Customize Toolbar..." and when the drop-pane opens, drag the icon
from the toolbar, and close the pane. It's gone.

--

-Jon Glass

At 00:54 -0700 UTC, on 2009-05-19, pmcclure wrote:

> I recently switched to IMAP (gmail, Mail.app, and iPhone) and have run into
>a problem I don't believe anyone has mentioned in this regard: if you read
>mail on your iPhone or google's web interface, when the messages are
>downloaded to your computer (assuming you are keeping copies there),
>Mail.app's rules will not be applied. Apparently Mail.app only applies rules
>to "unread" mail. Is that correct?

FWIW, I see the same behaviour with Eudora. Messages that I marked as read in
Eudora first, show up as read on the iPod touch, and the other way around.
Exactly as most people would want.

But the result is that, because Eudora's "Incoming" filters are only applied
to new *unread* mail, messages that I read first on the iPod touch aren't
filtered by Eudora. Sucks. I haven't found a solution yet.

Possibly the IMAP server can be configured to not let clients mark messages
as fetched. But I'm not sure how to do that with my server, and it would have
the side effect that a message you already read in one client, will still
show up as unread in another.

I suppose the only real solution would be for the client to apply filters to
new mail (messages it hasn't seen yet), but of course that's never going to
happen in Eudora.

The only workaround I can think of currently is to regularly run filters
manually. Eudora let's you do that. I've no idea if Mail.app does.


--
Sander Tekelenburg, <http://www.euronet.nl/~tekelenb/>

On Thu, May 21, 2009 at 12:23 AM, Joe Kissell <joetidbits.com> wrote:
> fcchuan wrote:
>
>      Just wondering, you set up IMAP like this, and have the IDLE preference
>      selected in Preferences --> Accounts --> Advanced, then what function
>      does the "Get All New Mail" command have in Apple Mail?
>
>
>
> It checks your mail, just like always! (And does so for all accounts, by the way.)
>
> For me at least, IMAP IDLE has never worked with Gmail and Mail. For example, if I enable IDLE support in Mail and set mail checking frequency to Every Hour, or Manually, and then go to another client and send myself messages, they don't arrive. If I check manually, or turn the schedule back on/up, they do. I've tested this quite a few times under numerous different conditions, and I always get the same result. So, I don't know if it's Gmail, or Mail, or something in between that's broken, but the only thing that has worked for me is automatic checking manually or on a schedule.
>
>      a.k.a. the Get Mail button in the toolbar. I know clicking on it causes
>      lots of activity in my Activity Window. But is clicking this button just
>      a bad habit from the POP days, and can I get rid of that button?
>
>
>
> If you set Mail to check automatically (anywhere from every minute to every hour), then you don't need to click that button. And if for some reason the button just really bothers you on the toolbar, you can remove it and use Command-Shift-N to check for new mail if needed.
>

Notice the wording in the preference pane checkbox for the IDLE
command: "...if the server supports it". So, the IDLE command may do
exactly nothing for a given server.

And it is described in RFC 2177 (unless there is a later one), not the
base IMAP RFC (unless I haven't found the newest IMAP RFC).

And the command means (rough paraphrase): "Server, you can send me
stuff when you feel like it, until I send you a DONE command." RFC
2177 gives EXISTS as one of the examples of responses the server might
give during an active IDLE. I haven't gone back and read about EXISTS.

In any case, IDLE not seeming to do anything is not wrong.

  --John

On May 19, 2009, at 3:54 AM, pmcclure wrote:

> I recently switched to IMAP (gmail, Mail.app, and iPhone) and have
> run into a problem I don't believe anyone has mentioned in this
> regard: if you read mail on your iPhone or google's web interface,
> when the messages are downloaded to your computer (assuming you are
> keeping copies there), Mail.app's rules will not be applied.
> Apparently Mail.app only applies rules to "unread" mail. Is that
> correct?


I don't have an iPhone yet :-( but I do check my mail on my office
[Vista-ugh] computer. I have found 2 work arounds. If I have only
checked a few emails then I tell them to show as unread before I log
out. That way they will go into the right box without me thinking
about it.
The second way is to select all the mail when it is downloaded to your
computer, then hold down the control button, and select apply rules. I
find this helpful when my internet connection is being a bit flakey
and the automatic sorting just doesn't happen.
I am using Mail in Leopard but it also worked in Tiger, at least the
later versions.
HTH,
Jean

I had that same issue and I think it has to do with pruning the IMAP folders in Gmail. What I did to finally fix it was (remember, this is IMAP, so deleting the account in Mail will not lose email) was delete that particular account from Mail and then I recreated it. It seems to be working so far, though the sync is not done.

Hope that helps!