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3rd party or "foreign" ISP. Outgoing mail - the definitive way to do it

It seems that over time the problem of sending email out through a "foreign" or "3rd party" connections (such as from hotels, etc.) has evolved and I'd like to see a rather definitive reference on the subject.

This is ONLY about using email client programs .. not about web mail please.

- It used to be that one could or would *have to* set up the outgong server in the email client program to match the ISP where you were connected at any time.
- It appears that either this was a misconception or has mostly gone away.  Now one can send mail "using" their normal "at home" ISP server settings in the mail client program.  It appears that all that's necessary is to have the "My server requires authentication" box checked and any login information included (which may simply be the same as the incoming login).

But, truthfully, I'm guessing at the latter.  So, I'd like to read something clear and definite about this.  It's obviously of great interest to travellers.
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Fred Marshall
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Fred Marshall
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3 Solutions
 
jeremycrussellCommented:
Back when you always connected to the internet through *your* ISP (dial-up connections) and they also hosted your mail, its was pretty simple, the SMTP servers only relayed mail for the network their ISP users were connected.  This day and age, an ISP has to consider that their users may have multiple devices using multiple ISPs, they can no longer really rely on their user having a single permanent connection to the internet.  So they, mostly, have evolved to use other methods to allow relaying of mail from thick clients over their SMTP servers, most notably simply using authenticated users.
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Fred MarshallAuthor Commented:
jeremycrussell: That's pretty much what I surmised in the question.  What I'm looking for is an authoritative reference to the "methods" that allow relaying ........
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Alan HardistyCommented:
The best option for mail when travelling is to use Outlook Anywhere / RPC Over HTTPS not SMTP / POP3.

The difference being that you are using TCP port 443 not TCP Port 25 / 110 and the logic behind this is that a lot of ISP's will block TCP port 25 (SMTP) to prevent the spread of email viruses that can spew forth spam if the port isn't blocked.

If you use HTTPS - no ISP will block this and as such, you can go literally anywhere and as long as you have internet access, your mail should not be stopped.

If this is not an option for you - then it is going to be hit and miss, or you need to use a VPN solution, assuming that the ISP or firewall in use in the premises you are located at allow VPN Passthrough.  This again may not always work, so the option of using Outlook Anywhere / RPC over HTTPS is usually the better (guaranteed) option.

Alan
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Fred MarshallAuthor Commented:
Well, it appears that Outlook Anywhere is a proprietary two-ended proposition.
What I have here is a variety of ISPs providing service to a variety of customers.  
And, what's needed is the most robust way possible to deal with those situations which are almost always POP3 / SMTP.
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Alan HardistyCommented:
If you are only able to use SMTP / POP3, then your best bet is VPN, but that isn't guaranteed to work as the IP range used at the remote site has to be different to the Exchange Server IP range and if the same, then it won't work.

If you can configure your mail client to send mail using a different TCP port e.g., 587, then that is more likely to work to a fixed server as long as the server is configured to receive mail on that port.

Port 587 is not likely to be blocked by most ISP's so that may be a better option, but again the firewall at the local site may not allow the port outbound, so you may still have problems in some locations.
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Fred MarshallAuthor Commented:
You can be very sure that the variety of ISPs providing mail service do not also provide VPN connections for the same purpose.

Indeed, one of the ISPs uses port 587 - but that's not a call that *I* make, they do.  It still raises the original question:
" It seems that over time the problem of sending email out through a "foreign" or "3rd party" connections (such as from hotels, etc.) has evolved and I'd like to see a rather definitive reference on the subject."
That is, it has evolved for the better and seems to be increasingly possible without changing email client app account settings (esp. servers, logins, etc.).

I had not mentioned Exchange Server at all.  So, that seems off topic.  Just to keep things focused.

I still have not received an authoritative reference - which is what I'd asked for:

"I'd like to see a rather definitive reference on the subject."
and
"What I'm looking for is an authoritative reference to the "methods" that allow relaying ........  "

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Alan HardistyCommented:
I am not sure you are going to get a definitive answer.  I have given you what I know based on 20 years of IT experience and 12+ years working with Exchange and Email in general.

If you want a working solution wherever you go - Exchange with Outlook Anywhere / RPC over HTTPS is your answer.  Anything else is going to be hit an miss.

Good luck.

Alan
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Fred MarshallAuthor Commented:
alanhardisty:  I'm unclear about your comments re: Outlook Anywhere / RPC over HTTPS as that approach appears to assume control of the mail server.  The cases I'm dealing with, there is no control over the mail server.  Can you please explain if I understand things incorrectly?
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Alan HardistyCommented:
Outlook Anywhere / RPC over HTTPS does require an Exchange Server and if you don't have one, then you might want to consider getting one so that you can avoid the problems of travelling and not being able to send mail, or utilising a 3rd party hosted solution which does provide this solution for you (most do) and that way, you get the benefits of Exchange plus the reliability of travelling anywhere globally and not having send issues in some locations.

Hosted solutions don't give you control of the server - it is just configured to work using Outlook Anywhere (Exchange 2007 / 2010), or if you have a host using Exchange 2003, then it is called RPC over HTTPS.  Either way, as long as the hosting company have this configured properly (it's not that difficult), then you have an easier life.

POP3 / SMTP and travelling generally don't mix well.
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Jamie McKillopCommented:
Hello,

I don't have a lot to add to what Alan has already told you but I will try to clarify some points. First, you need to understand that you don't have any contol over the networks you connect to and different networks have different security policies and allow different protocols. Due to the spread of viruses that send email, a lot of networks have port 25 blocked to anything except their own SMTP servers. This makes it virtually impossible to travel between various networks and expect to use your "default" settings in a POP client. Sometimes you can reconfigure your client to connect to a local SMTP server, sometimes you need to authenticate to relay and you may not have credentials. Setting up a VPN tunnel to connect to your home SMTP server is sometimes an option and sometimes it isn't, again, depending on the networks security policies. In the case of some hotel networks, they don't allow any traffic other than HTTP and HTTPS. You may be able to configure your SMTP server to listen for client connections on port 80 or 443, which would allow you to connect from vurtually anywhere but whether or not this is possible would depend on your server and how it is configured.

The reality is there are better options than POP3, which is why it is rarely used in a corporate environment. Webmail works in virtually 100% of all situations and is included in all modern email systems. I guarantee you will not get POP3 clients to work in anywhere near 100% of all situations.

JJ
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steveoskhCommented:
Fmarshall:  It may help us to know if this is:
A real problem situation, I.e, need reliable email when I travel.
Some type of academic question, research paper, exam, etc.
Or some other use, i.e., you want to know how to send spam from any hotel.

I list the last possibility because of clues in your reply.
 
"methods" that allow relaying ........
variety of ISPs providing service
sending email out through a "foreign" or "3rd party" connections
that approach appears to assume control of the mail server.  The cases I'm dealing with, there is no control over the mail server.

Now if getting a reliable way to send mail through a mail server you do not own or have permission to use, no one here is going to help you.

If that is not your goal, and this is not an academic exercise, please understand that we don't understand what you are asking.
For the most part sending mail is no longer a problem or issue as long as you are doing so under your own identity on a mail account you own.
 
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Fred MarshallAuthor Commented:
I'm sorry that the original post of the question wasn't clear...  So, I'll just answer the questions:

- This is a genuine question.  It's a little hard to imagine, given the introduction, that it would not be perceived as such.  But OK - it is!

- The question is limited to situations where the mail service is provided by a 3rd party, an ISP.

- The question is limited to situations where there is a mail client program in use.  No web mail.  Oh! But I already said that didn't I?

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"For the most part sending mail is no longer a problem or issue as long as you are doing so under your own identity on a mail account you own. "
If it's no longer a problem then why?  How is it accessed reliably or usually?

I have my theories (which I have stated) but I'd like to read an authoritative treatment.  Surely someone knows of such a thing or many of them perhaps?

Just to be very clear:

- Users have laptops.  They use Outlook (or maybe some other mail client program) and they use POP3/SMTP servers.  They travel around.  I find this to be a very normal situation.

- Users have ISPs that they are signed up with.  ISP at work.  ISP at home.

- Users find themselves in hotels, hot spots and homes of relatives where the ISPs are different than what they have at home or at their own office.  They want/need to continue to use Outlook without worrying about computer/account settings, etc.  

So, this *is* the "problem statement".  I'm not sure how to describe it better.  If there are additional questions I'll be happy to try to expand on this.  One might refer to the original posting of this question just in case....

For the most part this seems to work and I've said why *I* think it works.  But I'm not satisified that I have good enough information to provide rather decent guidance.  So, I want to read about it.

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Jamie McKillopCommented:
"For the most part sending mail is no longer a problem or issue as long as you are doing so under your own identity on a mail account you own. "
"If it's no longer a problem then why?  How is it accessed reliably or usually?"

I don't know where you are getting your information from but I don't believe it has gotten any easier to use a POP3 client while roaming. If anything, it has gotten harder as more admins start securing their networks.

"Users find themselves in hotels, hot spots and homes of relatives where the ISPs are different than what they have at home or at their own office.  They want/need to continue to use Outlook without worrying about computer/account settings, etc. "

There is no magic answer here that will apply to all situations. Sometimes everything will work perfectly without needing to change any settings, sometimes you can get things to work by changing settings, sometimes you aren't going to get it to work no matter what you do. The are just too many variables at play here. Bottom line is that there is nothing you are going to be able to do to get a POP3 client to work 100% of the time while network roaming.

JJ
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steveoskhCommented:
Sorry for the misunderstanding.  
I don't believe I will be able to provide anything new for you.  The others have already answered it.
Authenticated mail client and use the ISP web client as a backup.

@jjmck is correct that nothing will work always.  I have encountered my share of screwed up networks that did not work for anything.

If you have to have email, then a cellular card or smart phone is a good idea.
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Alan HardistyCommented:
In answer to the specific comment you made above:

"They want/need to continue to use Outlook without worrying about computer/account settings, etc."

The answer to this is an Exchange account (possibly Google Apps - never used it) with Outlook Anywhere / RPC Over HTTPS.  Anything else you try and do will be hit and miss because of the nature of POP3 / SMTP mail and Spam.

Like it or not - that is the best solution / answer you are going to get because there are inherent problems with SMTP / POP3 which I and others have outlined above for you.

If you want to have trouble-free emails from various locations without having to have users change settings, then I will repeat - you need to use Exchange (either hosted or in house) with RPC over HTTPS (if you have Exchange 2003) or Outlook Anywhere (if you have Exchange 2007 / 2010).

I would like to keep running a 1930's classic car and not have to keep taking it to the mechanic to keep it on the road and running smoothly, but the reality is that it is not possible.  Likewise, if you want your users to move from location to location and not change settings and not have problems sending / receiving their emails, then you need to change your way of sending / receiving emails.

I have my laptop configured in this way and visit all my customer's sites and simply hook up to their Wi-Fi or plug in a cable and I am instantly connected to my mail server and in flows my emails and when I send mail, it sends back to my server directly and then out to the desired recipient.  I don't have to change a single settings and never have any issues.

What you are looking for is a solution that simply doesn't exist the way you want it to work.

Alan
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Fred MarshallAuthor Commented:
We talked with our primary ISP who is serving up our email.  After reading the responses here and after that discussion, I've come to the conclusion that MY SERVER REQUIRES AUTHENTICATION for the outgoing server is indeed the approach that's recommended and seems to work for most users most of the time.  In fact, I've not yet seen a failure for this to work.  In honesty, I didn't connect "authenicated user" and some other comments until after some back and forth.  

Yet, nobody came forth with a pointer to any reference material which is what I was actually looking for / asked for.  But thanks for all the inputs!
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Alan HardistyCommented:
Good luck - it won't work in all cases, but then I've already mentioned that.

Alan
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