SSL or TLS via port 587 or 465?

Discussion in 'Email' started by Pennidren, Jan 18, 2010.

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  1. I am trying to use gmail's "Send mail through your SMTP server" feature such that when I send emails via gmail's webclient, my from address is shown as me@MYSERVER.com instead of "me@gmail.com on behalf of me@MYSERVER.com"

    As my lovely ISP blocks port 25, I am wondering if you support SSL or TLS SMTP on port 587 or 465?

    It seems that this is not the case as when I attempt SSL it says that it cannot reach MYSERVER.com. When I attempt TSL it says "Remote server does not support TLS code(500)"

    Has anyone had success using gmail like I describe? I searched the forums but since it seems that I cannot search on keywords of 3 letters or less (ie SSL, TLS, 587, 465), it was pretty painstaking! The only thread that seemed promising was this one, but there seems to be no resolution:
    http://community.discountasp.net/showthread.php?t=1945&highlight=gmail+smtp
    Perhaps this was never done? Based on this article, it sounds easy enough:
    http://www.smartertools.com/Portal/KB/a240/how-to-configure-ssl-tls-to-secure-smartermail.aspx
    But I know how "easy" easily becomes not so easy :)


    I am not a fan of the SmarterMail webclient. I heard it is improved in later versions. If I cannot get SMTP working through gmail, is there a chance that a newer version of SmarterMail is on its way?

    Thanks!
    Fred
  2. Bruce

    Bruce DiscountASP.NET Staff

    SMTP alternative port is 587 however, we do not support SSL.
  3. Nor TLS I suppose? Is there any chance that will be changing soon? Not to be a nuisance, but why no support for SSL?

    How about a newer version of SmarterMail?
  4. mjp

    mjp DiscountASP.NET Staff

    We don't support SSL for email mainly because there is not sufficient demand for it from our customer base.

    We have no plans to move to SmarterMail 6.x.
  5. Bruce

    Bruce DiscountASP.NET Staff

    SSL over SMTP in my opinion is not very useful if you want to secure your email.

    Think about this... SSL over SMTP simply secure the communication between your email client (Outlook, gmail or whatever) and our server. Once the messages gets to our server, it will be delivered to the target mail server using SMTP and likely be downloaded through POP3. BUT.... these connections are NOT secure. So what is the point of securing one leg of the whole journey.

    If you really want to secure your email, use PGP or something to encrypt the email. This will ensure end to end encryption.
  6. I totally agree with your encryption suggestions.

    I just want to use gmail as I describe and that seems to require SSL or TLS as I describe. Blame google I guess.
  7. I am having the same problem with gmail and SMTP with both domain accounts. So is this problem with Google or DiscountASP?

    Thanks
  8. mjp

    mjp DiscountASP.NET Staff

    Did you try the alternate SMTP port mentioned above?
  9. I cannot speak for SteveK but I did.

    Based on what I experience it sounds like Gmail will only allow use of port 587 with SSL or TLS.

    Problem is technically neither Google or DiscountASP, just orthogonal security philosophies.
  10. Same here

    I have the same problem. I created a ticket, but was told that it is a gMail issue. I beg to differ. I have set up SMTP account with gMail many times with many different servers, including GoDaddy, Nevidia, UplinkEarth, and more.
  11. mjp

    mjp DiscountASP.NET Staff

    It's not going to work here because, as bruce pointed out, we don't support SSL email connections. It is a Gmail issue insofar as they require SSL to send mail through your domain.

    But Pennidren hit the nail on the head: it is not really a Gmail issue or a DiscountASP issue. We just have different configurations and they are not compatible.
  12. Bruce

    Bruce DiscountASP.NET Staff

    Hello all.. i did some research on this topic and was able to create an asp.net page to send mail through Google.

    The key is you have to set EnableSsl to true.

    Sample code

    Dim mailMessage As System.Net.Mail.MailMessage = New System.Net.Mail.MailMessage
    Dim objMail as System.Net.Mail.SmtpClient = New System.Net.Mail.SmtpClient

    mailMessage.To.Clear()
    mailMessage.To.Add(New System.Net.Mail.MailAddress("Someone <someone@discountasp.net>"))

    mailMessage.From = (New System.Net.Mail.MailAddress("Some Name <email@gmail.com>"))
    mailMessage.Subject = "Test"

    mailMessage.body = "test"

    objMail.Host = "smtp.gmail.com"
    objMail.Port = "587"
    objMail.Credentials = new System.Net.NetworkCredential("someEmail@gmail.com", "password")
    objMail.EnableSsl = true

    objMail.Send(mailMessage)
  13. mjp

    mjp DiscountASP.NET Staff

    Sweet.
  14. A lot of us use GMail; please reconsider tweaking your SSL configuration

    Hello, I'm yet another GMail user that would like to send emails from my personal account hosted here at DiscountASP. As described above, GMail refuses to send emails through DiscountASP due to SMTP configuration incompatibilities.

    I'd like to add my voice to the thread to ask (beg if necessary) for a configuration change on the DiscountASP side.

    To clarify, we're not trying to send emails from our DiscountASP websites; instead, we're trying to use the GMail interface but send emails as if they originated from our DiscountASP-hosted domains (thus making GMail invisible).

    Because we can't do the direct SMTP sending, GMail sends emails "on our behalf"; in practice, this means that Outlook users see a crass "from peter@gmail.com on behalf of P Seale"), that I cannot subscribe to mailing lists with my real email address, and that people now know I have a gmail account and forget my true email DiscountASP-hosted email address.

    I have nothing else to add aside from the begging and whatnot above. For this message I've carefully chosen the most closely-appropriate emoticon to represent my ashamed begging. I don't think there's a "begging" emoticon outright, so I had to make do. -Peter
  15. ...On the Gmail site did you enable mail transactions?
    Look at the permissions there, it should work allowing your DASP mail to be forwarded through Gmail.
    All the best,
    Mark
  16. Wisemx, I don't think I understand your question. As is mentioned in the original post above, I can receive DASP emails in the GMail interface through their "check mail using POP3" feature. Sending emails, however, is the tricky part.

    I don't understand what you're asking. I've just re-checked the GMail settings for sending email and the first page of the wizard is as follows:
    --
    Send mail through your SMTP server?
    When you send mail as peter@dasp-hosted-site.com, the mail can either be sent through Gmail or through dasp-hosted-site.com SMTP servers.
    (o) Send through Gmail (easier to set up)
    ( ) Send through dasp-hosted-site.com SMTP servers (recommended for professional domains – Learn more)
    --

    I think the problem has been described in the original post above, but if you have fresh insight/a solution, I"m all ears.
  17. mjp

    mjp DiscountASP.NET Staff

    Has anyone suggested to Google that they change their configuration so as not to require SSL?

    No?

    A rhetorical question. Just making the point that since they are bigger, we are expected to change to accommodate them.

    Sorry. Still no plans to support SSL over SMTP.
  18. ...I may not be on the same page as you with this but what I meant is in the Gmail options there are some things you have to enable for go through to work.
    If this is a SSL problem, well, I have no idea. ;-)
  19. SSL over SMTP can be useful

    Hello Mjp. Your response surprises me. I cannot understand why you would be so sarcastic with your customers. gMail is a popular e-mail service that offers a lot of benefits to many small-to-medium businesses. Why does it surprise you that your customers would want use this service?

    As a hosting company, you also benefit when your customers use gMail. gMail helps to get e-mails that take up space off of your servers. It reduces your bandwidth since gMail users do not use your hosted SmarterMail service. I am sure these things add up.

    Also, I want to clarify the usefulness of SSL over SMTP. This is not just a philosophy issue, it is a security issue.

    SSL over SMTP encrypts my username and password between my e-mail client (Outlook, Thunderbird, etc) and your server. This can be especially useful for users who want to send mail while they are in a WiFi hotspot. Not supporting SSL means that your username and password are up for grabs when transmitting an e-mail message.

    SSL over SMTP does not just serve to protect the message (which you are correct about) - it protects the sender and your service from abuse.

    Finally, to answer your question. Many people do ask Google for features. Google makes it very easy for users to submit feature requests. If you ever want to add a feature to gMail, you can go here:

    http://mail.google.com/support/bin/static.py?page=suggestions.cs
  20. mjp

    mjp DiscountASP.NET Staff

    I am sarcastic sometimes, yes. I'm not sure where you got that I was surprised people wanted to use Gmail though. I use Gmail myself.

    I was, as I said, "making the point that since [Google is] bigger, we are expected to change to accommodate them," and I will take this opportunity to make the point again. We do what we do and they do what they do, and if the configurations clash, we are expected to make changes to accommodate them. My question is, and will always be, "Why don't you ask them to change?"

    What I'm trying to get across here is just because Google (or ATT or GoDaddy or anyone else) is bigger than we are doesn't mean that they know something we don't know. It also doesn't mean that we should change something that we do to accommodate something they do. That's all. Are there exceptions to that? Of course. I'm afraid this just isn't one of them.

    I know all the reasons someone might want to use Google mail, and I know why someone would want to use TLS or SSL over SMTP, but we don't plan to support it. bruce posted a workaround for mail sent form applications in this thread. That's the best we can offer right now.
  21. Same Old Same Old from DASP

    Lol, for starters, we wouldn't ask Google to change because (1) they are bigger, you are smaller, and thus should be more lean and able to make a change like this easier. However, (2) they are the standard, and have set it when it comes to email these days. You yourself acknowledged you use Gmail, and given that most likely the majority of your customers do, how about just trying to make your customers happy?

    I would venture a guess that you will see requests like this more and more, and maybe sooner or later you will decide to appease all of your customers who are requesting it.

    The fact is, your level of service is what I keep hearing as justification for the prices you all charge. Then I have a problem and I hear "we don't support that", or "go look in the forums", or better still, I read some smart a** reply from you. What a jerk.

    Just one more reason why I am done with DASP.
  22. mjp

    mjp DiscountASP.NET Staff

    When a significant number of customers want something, we always try to accommodate them. Unfortunately there are not a lot of customers asking for TLS/SSL for email. We simply cannot make global changes based on a small nuber of requests. We're not Google, but we're also not that small, and hundreds of servers can come into play when you start talking about global changes.
  23. Solution

    I guess the solution is for all users to speak up, and ask for TLS to be implemented.
    :(
  24. mjp

    mjp DiscountASP.NET Staff

    Well, it wouldn't take all users. When enough people want something we want to provide it, if it's at all possible. But if we did everything that everyone wanted us to do, the maintenance requirements would increase dramatically. If you want to maintain a high quality network (and we do) you have to say 'no' to some things.

    A perfect example is MySQL. When the company started we offered MySQL. But the demand for it was practically nonexistant, so we ended up with a MySQL server that very few customers used. It was an unnecessary piece of maintenance, and it required having someone on staff who knows what they're doing with MySQL. Even though no one uses it.

    So we took MySQL of the table. For a few years we did not offer it. But then, recently, more and more people started asking for it, because increasingly popular apps like WordPress require it. So we put MySQL back into the mix.

    When sufficient demand is there, we try to meet it.
  25. Just to chime in. I've been waiting for this feature for a long time now but was hoping it would eventually get implemented.

    Consider this another formal request for this feature.

    And to any lurkers out there that want this. Please spend the 10 minutes to create an account and log your request so they can tell how much demand there is for this feature.

    Also, while I agree that end to end encryption is desired for true encryption I think there is a middle ground where people think it's safer to have partial encryption in the local environment. Especially when roaming and using random wifi spots in the public and at coffee shops. It would be nice to know that my data isn't being stolen by people logging the traffic on these hotspots. I know the answer would probably be set up a vpn for real security back to the office but I'm not so worried about someone snooping my ISP back home as I am someone setting up a trap wifi network while traveling.
  26. I have also been waiting for this to be resolved.

    I've now given up waiting, and I wonder if you can guess whether I will be giving up my gmail account or my discountasp.net accounts?

    Points if you guessed discountasp.net!
  27. FWIW...The DASP Crew is currently working on upgrading the SmarterMail servers.

    btw, with a WP7 phone you can swim in all of the features of SmarterMail, Hotmail and Gmail effortlessly. OK, not everyone has one and it doesn't cure cancer, gasp, but I thought it was worth mentioning. ;-)

    *Smile and the World smiles with you.
  28. Do you have a ETA for the server upgrade, because I'd much rather stick with DASP if possible?
  29. No word yet but I'm drooling for it. :)
  30. Bruce

    Bruce DiscountASP.NET Staff

    we expect to start the upgrade in September.
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