IIS and Email?

Ok, this question simply dumbstruck me with its improper assumptions that I felt necessary to respond...


Hi, I just started working at a new startup company that does all their email via an IIS server, POPing into outlook express. I would really prefer to not have to use outlook express, but I can't find any way to have my email here forwarded to the email address I regularly use (someusername@gmail.com). Or rather, I can have outlook express do the forwarding, but then I still have to go to it, log in, and send/receive.

Is there any way to have our IIS server auto-forward my emails somewhere else?

thanks very much for any help


From a legal standpoint, I suggest you comply with your employer's configuration and use Outlook Express to check work email. The moment you work for someone else and handle someone else's property (email sent to your company account is company property, not your property), you have to play by their rules or else face consequences. Forwarding company property to an outside account is generally viewed as a no-no.

From a personal standpoint, I advise against using work email for personal use and vice versa. If you keep thing separate, it is much easier to organize your work/life balance. For example, if you leave the startup, you don't want your non-work friends still sending to your account at the startup. Likewise, you don't want your coworkers sending email to your personal account. Thus, I would never recommend the sort of forwarding that you are asking about.

I think you are trying to "organize" your life by having all email addresses forward email to one account so that you can check it all via one GMail client interface. Unfortunately, GMail does not support that scenario and probably never will. Why?

Because fundamentally, GMail is an email service with a web UI and NOT an email client. The sort of organization you want is best done with an email client like Outlook Express which can easily POP against GMail and any other POP servers and provide one consolidated view of all those accounts. Forwarding email around is just a horrible poor-man's hack.

For example, I run Outlook Express to get a single consolidated view of all my email accounts at yahoo, hotmail, and Gmail as well as Newsgroup posts. This is what email clients are good at; this is not what an email service does.

In other words, your desire to use GMail interface to check email has two major stumbling blocks:

  1. Your desire of user interface is irrelevant when it comes to corporate policy. If you don't like the policy, either get it changed or don't work there. If you violate policy, don't be surprised at the consequences.

  2. What you want to do is really not supported by GMail. GMail does not currently support POPping from other POP servers, which is what you actually want to do because you want to use the GMail interface but against non-GMail email source. I somewhat doubt this will ever happen because it would break search and other GMail features against the non-GMail email source.

Basically, since GMail does not support what you want to do, I think you started looking at other methods to get email into that account... and that was when you started wondering about forwarding from another POP client or forwarding from the SMTP server itself.

But since IIS has nothing to do with email (it is a web server), and I have no idea what your employer uses for SMTP server, I can only say that technically, the ability to Forward depends on that SMTP server's capabilities and your permissions to modify it.

But in your case, I suggest AGAINST what you are asking. Just check company email with Outlook Express like everyone else because GMail does not support your usage pattern. Your problem is really with GMail not supporting your usage scenario and not with any intervening client/server's ability to Forward email, so keep the solution in the same realm.


Comments (19)

  1. BlakeHandler says:

    Actually, Microsoft DOES have the instructions to use GMail with Outlook . . .


  2. The approach of using a single email reader for multiple accounts (Outlook in your case, Thunderbird in mine), is workable and – at least was – the best possible solution, it will not be the best solution going into the future.

    But … at this point I would not longer recommend this as the preferred solution. At base you do not want to run any application on the desktop for while there is a good-enough equivalent on the web.    For me GMail has finally crossed that threshold as a mail reader.  For work email (hosted on Exchange) Outlook Web Access is adequate (if less than great).  About the only time I fire up Outlook when I have to schedule a meeting – thankfully not often.  (Also of interest is that fact that even the current early form Google Calendar is decent – and groks meeting requests from Exchange.)

    Looking further out – if you can get the organization to change it’s ways – it no longer makes sense for a most companies to host their own email servers.  Google is working on a variant of GMail to host your company email.  You can support a fair-sized organization off an inexpensive web-hosting account.  

  3. segfault says:

    re: blakehandler

    That is for doing the opposite of what anonymous emailer wants to do…

    re: IIS and email

    First, a semantic point: there is some ambiguity about whether or not the smtp server is part of IIS or seperate from it. see:


    In response to the main point of the article, on the merits of forwarding email vs. a unified client approach, I don’t think its as clear cut as the case is presented.  Both methods have advantages and drawbacks and informed users can make personal choices about which they prefer.  (in case you disbelieve, the draw back to using a client to check all your emails is that such a client has to be installed and configured on every computer on which you’d like to recieve emails!  Forward all of your emails to a web service like google and it’s trivial to pop onto a kiosk at, say, the mall or library, and get a quick update from friends and colleagues both).

    Specifically, you imply that what the user desires is prohibited by his company.  I find this ironic in light of the opening sentance about assumptions.  You also assume that the user is going to go around giving his personal friends his work email; why you think he would do this I have no idea.

    Then you tell him his problem is ‘really’ with gmail.  The logic of how you arrive at this is, quite frankly, retarded.  Observe:

    1) Your solution is to work around Anonymous’ question by telling him to use gmail as a pop client.

    2) Gmail doesn’t have that feature.

    3) Gmail is the problem.


  4. Gabe says:

    I have a similar problem. I have a client using IIS (SMTP service) for their mail server. Every few months somebody will email me at the client’s domain instead of my gmail account. I’m not going to run Outlook Express constantly just so I can get the occasional misaddressed email, so it would be nice if there were an easy way to forward messaged.

    I’m thinking about writing a simple service to watch the server’s Drop directory and send the messages for me to my gmail account, but it would be nice if there were an easier way. I think that’s what the original poster was asking for.

  5. David.Wang says:

    segfault – the user wanted to use GMail as a pop client but can’t, so the user starts looking at email forwarding as a hack solution.

    The real problem is the user’s perception that GMail is a pop client when it is just an email service. But it is awfully harsh to tell someone who you hardly know "you’re retarded". Transforming that perception into a  feature request for GMail is a positive approach…

    For me, the "unified client" on a personal mobile device of various form factors like PDA, Cell Phone, or Laptop is the way to go. I only login on machines I control; I have no idea what shady software is running on a random kiosk.

    I am pretty certain my legal "assumption" is valid. If you find a company which does NOT have a policy which treats work email as the property of the company, they are either not yet legitimate or shortly will have such a policy. Just wait until you get a lawsuit and you will see what I mean.

    Ahh, I just love the different traffic that the word "GMail" brings…

    segfault, just chill – if you read the rest of my GMail references, you will see that I appreciate and love using GMail. You don’t have to jump down my throat and attack/insult me simply because I imply it needs improvement.


  6. James Vierra says:

    All right guys. You’re all right and all only partly right.

    1.  The default SMTP server on W2K and WS2003 are intended to be used for IIS web service to send email from a web site.  It is very light weight and not really good for corporate mail.

    2.  If you use OWA then Exchange is installed and forwarding is possible from the Options of OWA assuming Exchange 2003.

    3.  Exchange can grab external POP account mail with the POP connector for Exchange including gmail POP interface.

    4. Ther is no problem with running both a client like Outlook and the web interface.  I have been using both together for years from Hotmail, Exchange OWA and others.  I archive all of the mail at my Office with Outlook.  Never been a problem.

    5. If the forwarfing option is turned off on OWA then teh company has a policy to disallow this.  It’s not an OWA issue.  On older versions of OWA you need to ask the admin to set it for you in Active Directory.

    6.  SMTP is not part of IIS.  It is an IIS based application that comes with W2K, WXP and WS2003.  WS2003 has a simple POP manager.  All are optional and all are considered Windows add-in components.  IIS "Hosts" SMTP.

    7. Most corporations that are larger than 50 employees will either host mail internall or host it on Exchange at a hosting service.  Gmail wants a piece of this potentially large market.  So far their security record has taken a couple of bad hits.  When they recover from this they like OfficeLive, will be competing for corporate mail.  We’ll see.

  7. segfault says:

    Apoligies David!  The comments you take offense to were directed only towards the logic, not you personally.  After posting here I read several of your other posts and found them to be interesting and amusing (especially the one on job descriptions).

    My intention wasn’t to defend gmail (although i think its the best of the free web email services…. thats not saying much); rather I hoped to point out the way that you sidestepped the question in a manner that made it seem as if you were exposing some ignorance on the part of Anonymous emailer.  My thoughts when I first read the email from Anonymous and the following comments were something like this: "Thats a reasonable question.  Oh wait, its not a reasonable queston?  The emailer hasn’t got a clue? That can’t be right…."

    In short, I felt like your initial impression of Anonymous emailer biased you in your response.

  8. According to the Add/Remove Programs control panel, the SMTP service is a "component" of IIS:


    But SMTP is not used to store mail, only to send it where it goes.  In particular there’s no POP server that comes with IIS.

    But most POP servers allow some kind of automatic forwarding (via a server-side rule, or via a .forward file, etc.) so this should be feasible.

  9. James Vierra: WS2003 has a simple POP manager

    Maurits: there’s no POP server that comes with IIS

    … er, I should say, there’s no POP server that comes with IIS as of W2K.  Does the WS2003 MSA support automatic forwarding?

  10. David.Wang says:

    Maurits – It’s like ".NET". What is ".NET". Does ASP .NET have anything to do with the CLR or IIS. You see it in the control panel under one of them but is installed with the other…

    Treat technology as it is, not how it is marketed or positioned…


  11. Robert Spivack says:

    Interesting discussion.  I would like to point out the problem with one proposed solution – using Outlook Express (or Outlook) as a unified client to access mail from multiple services.

    You mentioned that one can use Outlook to pull in mail from yahoo, work, etc. yet you were quick to jump on the guy about violating his company’s email policy.

    I think you need to check your own (Microsoft’s) or any major company’s computer policy.

    STORING personal non-work related documents or information is usually a violation of most well structured (legally) policies for use of a company-supplied computer.

    The act of pop’ing Yahoo or other mail places personal, non work data on your computer.

    thus, other than your personally owned home computer, using a client as the unification point is typically a violation of company policy.

    Conversely, using a web-based email reader to pull in other email from pop accounts would be ok if teh web-based reader is not company supplied.

    Of course, from a legal standpoint, simply accessing a web-based mail reader to check your personal mail from any work computer, even though nothing "remains" on the computer (cleared cache, right) is still a violation of computer policy.

    Now, I wonder how many people that work at Microsoft are in daily violation of at least one of these computer use policies?

  12. David Wang says:

    Robert – uhh… sorry, you are assuming I am a hypocrit…

    I never suggested the user to consolidate personal email at work. I suggested:

    1. keeping the work and personel email separate

    2. for the user to check company email using Outlook Express as the company does because of the potential legal problems

    3. use an email client to consolidate access, not GMail since it is not designed for it

    Of course, I cannot speak for anyone else’s habits. I personally separate my work and personal computer activities, and I use Outlook Express to consolidate appropriately. Work related accounts stay at work and never accessed from home and vice versa. Yes, I do not even browse the web casually from work… I don’t have that time.

    So, I think I stand on pretty solid grounds here. It is just me and my suggestion since it was asked of me.

    You are always free to do what you want.


  13. Matt says:


    SMTP has been a part of IIS since IIS4. The first page of the IIS6 Operations Guide states:

    "Organizations of all sizes use IIS to host and manage Web pages on the Internet or on their intranet, to host and manage FTP sites, and to route news or mail using the Network News Transfer Protocol (NNTP) and the Simple Mail Transfer Protocol (SMTP). "

    The overview in the IIS4 Resource kit states:

    "IIS now includes a Simple Mail Transfer Protocol (SMTP) mail service that can send and receive SMTP mail messages"

    It’s not fair to just call it marketing or product positioning either – the SMTP Service (along with the FTP, NNTP and ,in the past, Gopher service) share much IIS operational and management infrastructure with the WWW Service – it’s one of IIS’s strengths.

    It’s perfectly reasonable to focus on the WWW Service in your blog but you do advertise it as an IIS blog. People looking for a place to ask an SMTP question might reasonably assume your blog might cover it unless they read through your archives.

  14. David.Wang says:

    Matt – uhh, yeah… can you please stop by and tell the IIS team that:
    1. SMTP is a part of it
    2. Exchange team does not own SMTP
    3. There is a new web server called “WWW Service”

    And somehow get us all into the same management division?
    Thanks a whole bunch. 🙂

    hehe… it is all HISTORICAL marketing and product positioning. Of course, you can feel free to trust the documentation folks to get it right; if I did, I would not be blogging (see my bio)…


  15. MG says:

    Though i might be deviating a bit from the core topic. I would like to know if there is a facility (gmail or email client or any software) that can now only consolidate mails from my 4 accounts but also ensure that when i reply to an email, the reply is sent from the email id on which the email was received.

  16. Alex says:

    Gmail does support popping.

    I may be mis-interpreting the problem here, but Gmail does let you get mail from external POP3 servers.

    It also lets you reply to messages with the receiving email address.

    Just to put the icing on the cake, Google also let you install the Gmail interface on your server, meaning all your email can stay in house, while you still have the GMail UI.

    So you can have your cake and eat it- use GMail UI, keep data on your company servers.

    And if folks still prefer thunderbird, Gmail also lets you access Gmail accounts with POP3 access from a client.

  17. IIS or not? Who cares! Arguing semantics to what end? It is more than appropriate to refer to IIS and SMTP together because that conveys to me EXACTLY which SMTP server is being discussed–there are many "SMTP Servers".

    The funny thing about this whole discussion is poor Anonymous’ question was never answered! So, maybe I can re-post it in a way that won’t cause all the above controversy:

    I am running a personal web site on IIS and want to forward all e-mail received for my domain to my personal Gmail account. I’d like to use Microsoft’s SMTP Server that installed by looking under the IIS options, manages through the IIS manager and has it’s "mailroot" directory inside the IIS "Inetpub" directory–yet, is apparently not a part of IIS. Is there a way to do this, or software anyone is aware of?

    (For what it’s worth, I don’t think "SMTP Server" can do this out of the box)

  18. Russix says:

    "Is there any way to have our IIS server auto-forward my emails somewhere else?"

    IIS is either dropping the mail into an Exchange Server or some other third-party POP server. I know in Exchange messages can be forwarded to an external e-mail address instead of being hosted in an Exchange mailbox. If you don’t have Exchange and your 3rd party POP server does not have the feature to forward your mail then you can write an IIS Event Sink in VBscript to catch mail addressed specifically to you and forward it to you.  

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