Will Exchange play nice with Gmail?

February 1, 2007 1:01 PM

Will I be okay having my work emails forward into Gmail?

Like many other MeFites, I am an avid Gmail user. Particularly it's the "conversation" threading that sets it apart for me.

At my new job (decent sized company, 250 or so employees, with an MIS dept and all that) there is an Exchange server and everyone uses Outlook (2003 I believe). I have not used Outlook that much but I used to use Outlook Express for my college email account via POP3, and I dread going back to the standard-pane-view-with-fixed-folders way of organizing email.

At my last job we had a more basic email system through our web host and it was easy for me to have this forward into a Gmail account and just use that. I am wary about doing this with my new work email becuase it appears that Exchange and Outlook are linked, and I know how difficult Microsoft makes it for their products to be compatible with anything else. Will I be able to use Gmail for my work email? Any tips or tricks? Will our MIS department get mad at me?

posted by radioamy to Computers & Internet (25 answers total)

I did this for about a year at my job, until it was mandated that I, and 5 or 6 of my like-minded colleagues, revert back to Outlook. Their argument was that if the company were ever sued, and an attempt was made to gain access to old e-mails (Enron, anyone?), Gmail would be much less interested in paying legal council to help protect the privacy of a user than would our own company. Plus they said it looked unprofessional.

Perhaps your question was of a more technical nature, but this is why my MIS Dept. got mad at me, so...
posted by M.C. Lo-Carb! at 1:14 PM on February 1, 2007

If you IT dept will let you forward all your mail you shouldn't have any problems. However, I bleive they control that ability in an Exchange environment. I use Thunderbird with our Exchange server without problem. For the rare occasion that I need to do something "Exchangy," like get into a public folder, I log in via Outlook Web Access.
posted by COD at 1:15 PM on February 1, 2007

"Will I be able to use Gmail for my work email?"

Sure, just set up some forwarding rules.

"Will our MIS department get mad at me?"

In all probability, yes. It's the kind of thing that will get you fired in some workplaces, so you should probably ask them about any policy they have.
posted by majick at 1:15 PM on February 1, 2007

Depends on your MIS dept and the type of information that would potentially be in your e-mail. In the banking industry, that would be a definite no-no, for example, because of potential personal information that could be contained in e-mail, and GMail not being on a trusted network.
posted by jferg at 1:16 PM on February 1, 2007

1) You're almost certainly violating a written company rule if your company is big enough to have an MIS. Don't do this. All that email is company property, and further if you auto-forward you will potentially be sending confidential information- at which point your job is possibly toast. It's also not inconceivable (though probably unlikely with 250 employees) that you won't actually be able to forward your email: either information rights management, or filtering rules on the Exchange server, could prevent you from forwarding internal email.

2) Maybe you should just go ahead and post the better question in this thread: "I am currently required to use Outlook with our Exchange server, but wish I could make it behave more like GMail's interface. However, I'm new to Outlook 2003 and how much richer its features are than Outlook Express. Please help!"


I'm not meaning to be snarky but Outlook is, I think, an amazing product, and one of the best MS has ever made IMHO. It also is very customizable in a number of ways, and if you want a conversation view for example that's already built in. There are so many things you can do with Outlook, including filters, presentation, auto-storage, auto-sorting, and different views, that I actually can't understand why you'd prefer GMail.

I'll boldly state that there is probably nothing you're doing in GMail that you couldn't also do in Outlook- along with much much more. You just need to ask how. :)

So- what's the thing you want Outlook to do?
posted by hincandenza at 1:39 PM on February 1, 2007

Response by poster: Hmm... I never thought about it violating company policy...I do PR for a blood bank.

hincandeza, how could I set up conversation style? I don't like having to flip back between sent-mail and my inbox, and having to search around the inbox for original messages, etc. What are some other cool things about Outlook? I'm intrigued.
posted by radioamy at 1:46 PM on February 1, 2007

As long are you are using Outlook 2003, you will have an "All" folder. Use this as your default view, and sort by conversation.
posted by kellyblah at 1:57 PM on February 1, 2007

IIRC, GMail's terms of service include a clause to permit Google to read your mail and use the contents of it. They're using it as part of their ongoing efforts to organize and understand the web, so they look for URLs and text descriptions of those URLs in GMail just like they do the websites their spider visits.

Probably not a good idea to have corporate email, which may contain proprietary information, held on a public email server whose owner reserves the right to read and use it for their own purposes.
posted by Steven C. Den Beste at 1:59 PM on February 1, 2007

Also, it's not like gmail is the only thing out there with a search function... though gmail evangelists may imply that. Outlook's search function has never done me wrong.

I don't love Outlook either, because it's MS and because I don't top-reply to my personal email (and Outlook makes it painful not to), but it's way easier to adapt to its use in your organisation than to try to fight it. Particularly if there is also heavy reliance on shared calendars, meeting invitations, and the like.

To use conversation threading follow instructions here.
posted by loiseau at 2:01 PM on February 1, 2007

Well, for starters you'll want to look at the View menu- you can choose Arrange By- and choose to group by conversation (or click on the Subject field in the mail view). You'll also want to go into your Tools -Options- Preferences- Email Options and choose to save any sent messages in the same folder as the message you're replying to- this will keep mail "threads" together nicely.

In addition, you can still filter your mail into subfolders via inbox rules- but, you can then create Search Folders that will display any mail anywhere in your Mailbox that fits certain criteria- unread mail, mail from people, mail of certain size or date, even just "all mail" etc- and then that "folder" becomes a virtual view of items scattered around your inbox- which you can similarly view by conversation, etc.

Try those for starters, and also check here for some helps/how-tos and beginner information. I have to run to some afternoon meetings, but feel free to post other things you'd like to do, and I'll reply later with some tips.
posted by hincandenza at 2:08 PM on February 1, 2007

oddly enough, I just set this up today:

I have a webmail from my ISP with a typically slow and unreliable interface. I set it up so I can send right from gmail and it appears to be coming from my other email. And anything sent to the other address shows up in gmail.

The only drawback is that if anyone actually takes a lcose look at the headers, it'll say 'sent by gmail." But how many people do that?
posted by drjimmy11 at 2:09 PM on February 1, 2007

re: loiseau: Outlook's search "ability" is the main reason I switched to Gmail. It takes minutes to search for anything.
posted by null terminated at 2:12 PM on February 1, 2007

A couple of things:

"The only drawback is that if anyone actually takes a close look at the headers, it'll say 'sent by gmail." But how many people do that?"

Actually, Outlook 2007 (and maybe 2003) will say "[e-mail] On Behalf of [e-mail]" (or the other way around), so it will be clear to anyone using Outlook that you're using GMail's "Send As" feature.

For search, Outlook's search in 2007, with the integration with Windows Desktop Search, is about on par with Google's. The drawback, of course, is having to have the Desktop Search installed too, which can hog resources occasionally. In 2003, it was way slower than GMail's, but things like LookOut and, again, Desktop Search can make that a little better.

When I had to use Outlook, I also missed the threaded conversation view in GMail that included by Sent Mail, and the best solution I found was to set up a rule for outgoing mail that moved the message to the Inbox, so both the original message and my reply would show up in the threaded view - something you might try if that's what's keeping you from using Outlook.
posted by mikeyk at 2:24 PM on February 1, 2007

I don't know the business (or jurisdiction) you're in, but I would expect to be sacked for the near-certain breach of the Privacy Act which that would entail (though I wouldn't expect to end up paying the huge fine that I almost certainly deserve).

Probably worth thinking about.
posted by pompomtom at 2:30 PM on February 1, 2007

You work in PR and you're thinking about having your emails sitting on a server that your company can't control?

I'll have to echo almost everyone else here: bad idea, could cost you your job.
posted by dirtynumbangelboy at 3:04 PM on February 1, 2007 [1 favorite]

Even if it were allowed, I still wouldn't do it. It looks unprofessional as has been said before.
posted by grouse at 4:11 PM on February 1, 2007

Don't do it. I work in IT and we have had the unfortunate task of providing evidence to HR and external auditors that sensitive information was sent to an external mail provider and subsequently lost (with questionable results afterwards).

A forwarding rule was determined to be the cause and the person was not only fired, but sued as well. Obviously, I was not privy to the outcome but it doesn't sound like something I would risk.
posted by purephase at 6:16 PM on February 1, 2007

Do it until they tell not to, then don't ever do it again.

probably the most important thing I ever learned on my leadership course, bar none
posted by furtive at 7:54 PM on February 1, 2007

radioamy: What are some other cool things about Outlook? I'm intrigued.

One thing that attracted me from the start was the three vertical panes; folders, messages and preview. It allows me to read, scan and sort email without switching views and I'd love Gmail to have something similar. (Seriously, I'd consider moving from Gmail to Windows Live Mail for that feature alone.)

I use Gmail exclusively for personal mail and Outlook 2003 at work. I'm also a Free (libre) software enthusiast with no great love for Microsoft. It frustrates me that the Free Software world sneers at Outlook, rather than learning from its usability and general design.
posted by Busy Old Fool at 7:50 AM on February 2, 2007

I have a tip for those who want to use Outlook conversations and see their sent files at the same time.
Instead of copying all sent files or cc'ing yourself (a real problem if you have a small size limit on your mailbox like I do), create a custom search folder. You can set up the search folder to search for everything in the inbox, sent folder, and (if you really want Gmail style) an archive folder. Then set the view of that search folder to be grouped by conversation, sorted by unread then date, and with the "in folder" column visible. Add the search folder to your favorites, and then you can have a one-click way of getting to the Gmail view.
posted by buildmyworld at 9:59 AM on February 2, 2007

That's a good tip buildmyworld, except, um... :)
posted by hincandenza at 10:09 AM on February 2, 2007

Am I missing something here? I've tried a large sample of these recommendations, and none of them makes Outlook looks like GMail. Gmail lists my conversations do that the most recently active one is at the top. In Outlook 2003, if I group-by-conversation, I get the sorting in alphabetical order of the conversation title. If a new email gets added to the thread, it is buried way down - which is useless. I can't combine group-by-conversation with sort-by-received-date (except that within a conversation group, the latest received will be at the top). I must be missing something!

Buildmyworld's search-folder tip is great, because all the other recommendations for incorporating Sent emails into the conversation group involve irreversible changes (eg copying/moving) to folder contents.
posted by mediaddict at 11:42 AM on February 2, 2007

Okay, again- not to be too petty- but I made the search folder suggestion well before buildmyworld. mediaaddict: if you found the previous links unhelpful, then do this:

Create a GMail view folder
1. In the left hand Navigation pane, click on the "Folder list" button. Now, you should see the Search Folders in your list of folders.
2. Right-click on Search Folders, and choose "New Search Folder". Don't specify any Criteria- just give it a name like "ALL MAIL" or "GMAIL VIEW". You could add criteria to make your life a little simpler in this view, such as only mail from the last 3 weeks, or mail that's not in your Deleted Items folder etc, but the default- to see your entire mailbox- would be using no criteria at all.
3. Go to your All Mail folder, and choose View -> Arrange By -> and Custom, uncheck the "Automatically group..." box and then choose Group by "Conversation" ascending, then by Received Descending", then click OK and choose "Sort..."and set to sort by Received descending.
4. I'm not 100% sure if this will help make the view more or less Gmail like, but apparently under "Other Settings" in the custom view dialog, you can uncheck the "Sort by Groups".

The above will create a view that is very GMail like. Not quite perfect in its sorting? Then play around with the group by and sort by Options in the Custom view dialog box. Now let's set this as your default folder on startup:

Making this view your default view
1. Go to Tools - options - Other -> Advanced options. and at
the top where it says "Startup in this Folder, browse to the new All Mail folder you created, then click OK
2. Still in the Tools -> Options window, go to the first tab, Preferences, and choose Email Options, and Advanced Email Options, and choose the "In folders other than the Inbox, save replies with original message"
3. On the view menu, set the Reading Pane to Right or Bottom, as you desire
4. Also on the view menu, de-select the Navigation Pane.

This will have the effect of making the All Mail view your default view at startup, and hiding the navigation pane, so you have a single-view of your entire mailbox. You can always get your Navigation pane back from the View menu.

In addition, you can do cool things with automatic formatting- for example, I like to go to the Customize Current View and create a new Automatic Formatting rule that makes the font for the mail a little larger, and different color, if my name is on the To line- this helps so that when a mail is sent directly to me, it's that much more visible from the usual crap that gets sent out to broad aliases. You should still use sorted folders and mail rules (under Tools and Alerts) to organize your mail into folders, such as mail from your teammates, mail from Distribution lists, etc- but this will just help in organization and storage, while your "All Mail" view will give you an easy GMail like interface.


Now, I'm not a GMail user, so if that's not quite exactly how GMail works- well, then that's a minor detail. The point I tried to make earlier still stands: that with a little experimentation on the Custom view, you can almost certainly do exactly whatever it is you're wanting to do, and then some. Outlook's set of rules and flexibility make it incredibly powerful.
posted by hincandenza at 2:48 PM on February 2, 2007

hincandenza: my apologies, I followed the "um" link after posting. You get full credit.

OK. I've followed your very detailed instructions - thank you - and tried the various options:

View => Arrange by => Custom... - Group By...: the various choices are: [check/uncheck] Automatically group according to arrangement; and, Group by Conversation, then by Received, both Ascending or Descending - all can be combined in various ways.

Case 1) Group by Conv (desc), then by Recv (desc)
- this sorts by conversation, but a newly-arrived email is buried in the middle of the heap of old emails - my biggest problem.
- changing Sort... by does not change the appearance at all, whether you choose Recv or Conv.

Case 2) Group by Recv (desc), then by Conv (desc)
- this is similar to simple sorting-by-Received in that it does not actually group by conversation, even if two emails in the same thread arrived on the same day! It looks much worse than simple sorting-by-Received because it tries to group, but each group contains only one email. (very wasteful).
- changing Sort... by does not change anything

Regarding your first item 4): Other Settings contains a "Show items in Groups", but I do not see a "Sort by Groups".
View => Arrange by => Custom... - Other Settings -> Show items in Groups is the same setting as View => Arrange by => Show in Groups. Check/unchecking it does not change the appearance at all.

I believe I've explored the whole phase space, and I have not been able to get the GMail-like behaviour I seek - most-recently-changed-conversation-at-the-top-of-the-list. I'm generally OS-agnostic, but my opinion of Outlook has degraded with this bit of experimentation. Most of the phase space I explored was visually unusable, and half of the selectable options had no effect and should really have been grayed out to reflect that.
posted by mediaddict at 2:55 PM on February 5, 2007

Oh well- it seemed to work for me, so not sure what to tell you.
posted by hincandenza at 9:38 AM on February 6, 2007