Travel Technology - Internet access providers in hotels who block sending through Outlook - annoying!

I'm in a Le Meridien right now, and they have Inter-Touch as their internet access provider. I wanted to send some e-mails, as many business travelers, I use Outlook for that. Once again, I have the problem that the access provider apparently blocks the SMTP port or something like that (I don't know if I am expressing that correctly - but the fact is that all the e-mails are stuck in my outbox).

This is annoying!!

What do these operators think? Isn't sending e-mails one of the things business travelers would do?? Why do they block this?

This is ridiculous.

What would you do, other than complain to the hotel and suggest they switch their provider?

... wanted to send some e-mails, as many business travelers, I use Outlook for that... but the fact is that all the e-mails are stuck in my outbox).
....
What would you do, other than complain to the hotel and suggest they switch their provider?
Try Thunderbird and see if it works for you.

I used to use Outlook as well. Never had any problem receiving or sending email at home until my university upgraded the security measures 2-3 years ago, due to a security breach. Suddenly, I couldn't send email no more (from home). :eek: I am no geek but am very capable following IT instructions and do it myself. I got to our IT website and set up my mail client (Outlook) accordingly. Still no outgoing capacity. Then I took my laptop to our IT support and had them do what I had done (mail server, authentication...etc) all over again, still no go. Was told it's my ISP's issue and I needed to contact them to get the proper config for outgoing mail server and to open the SMTP port or something. Did that, still no good. So frustrating. :(

Then I decided to try Thunderbird, thinking what I had to lose? ;) IT WORKED FLAWLESSLY on my 1st try! Once I tried Thunderbird, I never went back to Outlook. :D Not sure if your issue is the same as mine. To be honest, I still don't know why Thunderbird solves my outgoing mail problem (i.e. same ISP, same mail servers..etc).

Anyway, give Thunderbird a try.

It isn't always the hotel's ISP doing it; it could very well be your own.

Most ISP's block relaying from outside of their own networks, as uncontrolled relaying of SMTP is one of the primary enablers of SPAM.

My home-office ISP does this, but I also have a GoDaddy/SecureServer account that requires authentication and runs on a non-standard (for SMTP) port that is rarely blocked by outbound rules on any firewall.

Before I obtained my SecureServer account, I tunneled SMTP over ssh to a Linux host on my home network. Through this box, the SMTP connection was port-forwarded to my ISP's SMTP server. My outgoing email therefore appeared to come from within my ISP's network and was properly delivered.

I have the problem that the access provider apparently blocks the SMTP port
That's pretty much it. They are blocking connection attempts to e-mail server's SMTP port.

Why do they block this?
Spam. Blocking outgoing connections prevents spam e-mail from becoming internet traffic in the first place. Additionally, if the ISP does not address the spam generated by their customers, their e-mail can get blackholed.

There are many ways to work around this problem. The preferred method is to use VPN to connect to your workplace's intranet. All of your traffic will be encrypted and bounced through your workplace before reaching the internet. I would do this any time I am not directly connected to my office network.

The other option is to use SMTP over SSL, which uses a different port number as SMTP. Your e-mail is also encrypted in this method.

I'm in a Le Meridien right now, and they have Inter-Touch as their internet access provider. I wanted to send some e-mails, as many business travelers, I use Outlook for that. Once again, I have the problem that the access provider apparently blocks the SMTP port or something like that (I don't know if I am expressing that correctly - but the fact is that all the e-mails are stuck in my outbox).

What would you do, other than complain to the hotel and suggest they switch their provider?

My ISP at home blocks the SMTP port (25), so that generally restricts users to using their mail server. The ISP probably provides their own SMTP mail server, if you can determine what that address is, you can temporarily change Outlook to use it for outgoing mail. It is often something like MAIL.<domainname> or SMTP.<domainname>.

I just checked this (http://www.inter-touch.com/cs_faqs_bt.php)page at Inter-touch's site, and this would imply that they are not doing any blocking, but that you need to accept their T&Cs before sending email:

Will I need to change my computer settings to use the interTouch system?

The interTouch solution has an unprecedented ability for getting guests connected on the first attempt without the need to make any alterations to their computer settings. However, should you encounter any problem in using the interTouch system, our Customer Support Service is available 24 hours a day, 7 days a week.

Do I need to re-configure my email application to send mail?

No. The interTouch system is compatible with your Internet Service Provider (ISP) or company email system and should work with your current configuration settings.

Note: You can only send and receive email after accepting the interTouch purchase terms from within your Internet browser.

As others have pointed out, its not so uncommon a thing. Either through local port blocking or closed relays from your ISP...

There are a few things you can do.

1) use a web client - not always optimal but remember that you outlook will sync up when you get home

2) use a 3rd pary SMTP server such as GMail...with a gmail account, you authenticate to the outgoing server so they don't consider you a spam risk. By making sure your "reply to" address is correct then messages will appear to come from your Home ISP account

3) Use a VPN - I tend to get a bit soapboxy about this point around here, but I always recomend a VPN connection when traveling. The benifits are many, not the least of which they help protect you from the prying eyes of other hotel guests. Whe a VPN connection you should be able to reach your home ISPs SMTP server just like you were at home

Does your company have Outlook Web Access set up?

For those that have switched to Thunderbird how is the add-on calendar program? I liked Thunderbird but couldn't live without the integrated calendar... now that it is all in one, does it work well?

I would have to sync to a Nokia e61, hopefully that wouldn't be an issue.

For those that have switched to Thunderbird how is the add-on calendar program? I liked Thunderbird but couldn't live without the integrated calendar... now that it is all in one, does it work well?

I would have to sync to a Nokia e61, hopefully that wouldn't be an issue.

Thudbird + Lighening works quite well. I prefer iCal on my mac, mostly because it plays so well with my e61i

Before doing the gmail option's smtp, this little program worked quite well

http://www.softstack.com/freesmtp.html

I think the easiest and really the most secure is to setup SSL if your provider has that ability and a lot of them do now for security as well as the issue that you are facing.

I have never had problems having the hotel internet provider giving me a server to bounce mail from on their network back when I didnt use SSL. I did have a provider in Rome that did not have a server that was allowed to send mail out so I was SOL there but I was surprised that everyone that I asked provided a relay server for me.

I would try to get SSL setup though.

With Outlook, if you are connecting to an Exchange server (eg at your office) there might be another problem - hotels sometimes block the port Outlook uses for this. You can overcome this by selecting an option "Connect to my Exchange mailbox using HTTP". It's deep inside some options in the mail setup, hidden very well.

With Outlook, if you are connecting to an Exchange server (eg at your office) there might be another problem - hotels sometimes block the port Outlook uses for this. You can overcome this by selecting an option "Connect to my Exchange mailbox using HTTP". It's deep inside some options in the mail setup, hidden very well.

The fact that my company is using an MS Exchange server means I cannot just decide to switch to Thunderbird, etc. I was led to believe that it's Outlook only.

I always use a VPN to connect to my company, as I work from home when not on the road. We used to use the Checkpoint VPN. Always worked from home - I mean 100% of the time. Also worked from most hotels. Every once in a while, there would be a hotel where Outlook would not connect. The VPN seemed to connect fine, but Outlook would never connect and sync. This is with a VPN. Exact same connection method used at home. For example, I stayed at the Marriott Courtyard in Edmonton probably a dozen times - never got an Outlook connection while staying there. Always had to use Web-based mail.

Any ideas as to what the hotel ISP could be doing that could block connectivity through a VPN?

We no longer use a VPN, and have now switched to PPTP connections. Have not had any problems at hotels, yet.

We no longer use a VPN, and have now switched to PPTP connections. Have not had any problems at hotels, yet.

PPTP is a type of VPN, but that is just a semantics thing.

If you are connected via VPN to the home office and Outlook can't connect to the Exchange server the issue is almost always DNS resolution. Your Outlook account is looking for a server named EXCHANGE01 or something and that only works if your computer asks a DNS server in your office for that name. If the laptop asks a DNS server provided by the ISP (which isn't uncommon in the situation you're describing) then the Outlook client won't find the Exchange server and that will prevent you from connecting. The easiest way to fix this is using a static setting in the hosts file on your computer, but that requires some additional knowledge to set up.

There are things that hotels can do to prevent you from connecting to a VPN at all, though you'd know pretty quickly from the VPN client if that were happening and I assume it is not the case here.



You can overcome this by selecting an option "Connect to my Exchange mailbox using HTTP."
This setting requires configuration server-side as well as a patch to be installed on older versions of the Outlook client. It is not always possible to use it. That being said, the setting is under Tools | Email Accounts | Change/Modify | More Settings | Connections. At the bottom of that window you might see something about RPC/HTTPs; it is only available in Outlook 2003 and 2007, not Office XP. If you can get that far, put your Outlook Web Access server address in the box. It might work and it might not. If it does, your IT people have set you up for the best connectivity option for Exchange possible anywhere. I used to have it at my job and it was phenomenal. "Normal" Outlook access without a VPN or any other special steps to set things up.

The fact that my company is using an MS Exchange server means I cannot just decide to switch to Thunderbird, etc. I was led to believe that it's Outlook only.

I always use a VPN to connect to my company, as I work from home when not on the road. We used to use the Checkpoint VPN. Always worked from home - I mean 100% of the time. Also worked from most hotels. Every once in a while, there would be a hotel where Outlook would not connect. The VPN seemed to connect fine, but Outlook would never connect and sync. This is with a VPN. Exact same connection method used at home. For example, I stayed at the Marriott Courtyard in Edmonton probably a dozen times - never got an Outlook connection while staying there. Always had to use Web-based mail.

Any ideas as to what the hotel ISP could be doing that could block connectivity through a VPN?

We no longer use a VPN, and have now switched to PPTP connections. Have not had any problems at hotels, yet.

On Checkpoint, look at your VPN connection type. In addition to standard connections, there is one called tunnel that is enabled on many systems. It pushes the entire net through the tunnel and also uses a method of connection which works a little better in some cases. I agree with you, however, a business hotel has no business blocking VPN connections.

If you are connected via VPN to the home office and Outlook can't connect to the Exchange server the issue is almost always DNS resolution. Your Outlook account is looking for a server named EXCHANGE01 or something and that only works if your computer asks a DNS server in your office for that name. If the laptop asks a DNS server provided by the ISP (which isn't uncommon in the situation you're describing) then the Outlook client won't find the Exchange server and that will prevent you from connecting. The easiest way to fix this is using a static setting in the hosts file on your computer, but that requires some additional knowledge to set up.

Go ahead, hit me with it! I can modify my hosts file (I have in the past), but I don;t remember where it is! It's something you touch maybe once every two years, so I always forget...

Anyway, if my laptop is always asking the ISP's DNS server for my Outlook server, why would it work at home (ISP is Comcast), but not in Edmonton (ISP is ???)?

This setting requires configuration server-side as well as a patch to be installed on older versions of the Outlook client. It is not always possible to use it. That being said, the setting is under Tools | Email Accounts | Change/Modify | More Settings | Connections. At the bottom of that window you might see something about RPC/HTTPs; it is only available in Outlook 2003 and 2007, not Office XP. If you can get that far, put your Outlook Web Access server address in the box. It might work and it might not. If it does, your IT people have set you up for the best connectivity option for Exchange possible anywhere. I used to have it at my job and it was phenomenal. "Normal" Outlook access without a VPN or any other special steps to set things up.
Did not work for me. The settings were there, and I changed them to match your description. I then dropped my PPTP and restarted Outlook. It could not connect - it gave me a little login/password window, but never connected after I entered my information.

With Outlook, if you are connecting to an Exchange server (eg at your office) there might be another problem - hotels sometimes block the port Outlook uses for this. You can overcome this by selecting an option "Connect to my Exchange mailbox using HTTP". It's deep inside some options in the mail setup, hidden very well.
Thanks for the tip. I replied in another posting that I was able to change my Outlook settings to match this, but it would not connect to Exchange. Apparently additional configurations must be made on the Exchange server to make this work - configurations that my company must not have implemented.

For communication from Outlook to the Exchange server, does that use the standard SMTP port, or a different port? If a hotel is blocking the Outlook-to-Echange port, is there a way to use a different port temporarily?Or would this also require server-side configuration?

I love talking about this stuff!

I've seen this problem a couple of times on the road. My solution is to temporarily change from port 25 to port 587. Seems to work.

As others here have said, the problem arises from the fight against spam, botnets and other malware. The operators of public networks have to take increasingly drastic steps to restrict what can be done on their networks.

This arms race creates a serious problem for most business travelers. When we try to send e‑mail using our customary tools, we get a message that can range from merely uninformative to mystifying.

There are some options to solve this:

- reconfigure your e‑mail program whenever you are on a new network (in a new hotel, for example),

- reconfigure your e‑mail program to use authenticated SMTP and an alternative port (like port 587 instead of port 25), if your ISP offers that option,

- use web-mail, or change to Google Mail or Yahoo Mail

- install your own SMTP server on your laptop,

- install a Virtual Private Network (VPN)

- use a purpose-built tool like LoaPost - http://www.loapowertools.com - that costs a bit, but doesn't need to be changed or fiddled with. I have to confess to a connection to Loa, so apologies for the commercial. But I do think this is useful.

- use web-mail, or change to Google Mail

I use Google Apps for Domains and it gives me an smtp server that I can use. So the web interface isn't necessary.


- use a purpose-built tool like LoaPost - http://www.loapowertools.com - that costs a bit, but doesn't need to be changed or fiddled with. I have to confess to a connection to Loa, so apologies for the commercial. But I do think this is useful.

Seems rather pricey? And I assume it works pretty much the same as the Free SMTP server I linked to above?

What does it have/do that that program (or other localhost smtp programs) doesn't do?

I use Google Apps for Domains and it gives me an smtp server that I can use. So the web interface isn't necessary.



Seems rather pricey? And I assume it works pretty much the same as the Free SMTP server I linked to above?

What does it have/do that that program (or other localhost smtp programs) doesn't do?

Good question, and I'm a little reluctant to give any more of a commercial than I already have, so as not to abuse this forum. But the simple answer is that LoaPost is not an SMTP server like either of the ones you mention. Nor is it a relay service. That's because running your own SMTP server on your laptop has a few disadvantages.

1. You still need to get out from behind the hotel's or the airport lounge's or the café's or other hotspot's firewall and around the restrictions in place from the ISP that is providing service to the hotel or lounge. And as the Anti Spam Technical Alliance (and others) are recommending, most ISPs and network operators will close outbound Port 25. See http://www.postmaster.aol.com/asta/proposal_html.html . They may or may not keep other ports (like 587) open - some do, some don't. So you are faced with uncertainty about whether you will be able send your email. And when you are on the road and in a different hotel every night and several airport lounges each day, uncertainty about whether you will be able to send your mail is not much different from not being able to send.

2. To attempt to contain the botnets, network operators are increasingly refusing email that originates at dynamic IP addresses that are not on their networks. When you are traveling, your laptop almost certainly has a dynamic IP address, so the email that you originate from the SMTP server running on the laptop is likely to run into blockages.

3. Some people, and you are among them, are capable of and comfortable with administering an SMTP server running on their own laptop. SMTP, as you may have found from your experience, can be a fairly complex protocol when you get beyond any but the most normal of situations. And the wild world of wireless networks in hotels, airports and cafés (which may have been installed by a technically competent organization but are often left to be administered by an amateur) is often pretty non-normal.

4. I should add something about security. Mail sent using an SMTP server installed on your laptop goes out in unencrypted plain text over the Internet, over the corporate network of the client you're visiting or in most hotels and airports these days, over a wireless network. Mail sent with LoaPost is encrypted to very high standards.

- use a purpose-built tool like LoaPost - http://www.loapowertools.com - that costs a bit, but doesn't need to be changed or fiddled with. I have to confess to a connection to Loa, so apologies for the commercial. But I do think this is useful.

I use Google Apps for Domains and it gives me an smtp server that I can use. So the web interface isn't necessary.


Seems rather pricey? And I assume it works pretty much the same as the Free SMTP server I linked to above?

What does it have/do that that program (or other localhost smtp programs) doesn't do?

I, too, was rather skeptical of the Loa product. I actually called kgord out privately for his sales pitches here on FT. That being said, I do see situations where such a tool could be useful.

I routinely configure networks at my client sites to block all outbound port 25 traffic from any machine that isn't a known mail server that is supposed to be connecting to the Internet. This is done so that even if someone manages to get a mass-mailer app installed on their computer on the network the company is not blacklisted for spamming. This and bandwidth usage are the main reasons that local connectivity providers will block outbound port 25 access. Configuring your system to use an alternate port is fine, but the maintenance/configuration work on the client side is higher, which is something most admins try to avoid. Plus, it is basically security through obscurity. A decent firewall with packet inspection will determine that you're sending SMTP traffic and shut it down if that is the policy. In this sort of situation the Google SMTP server would remain inaccessible to you.

From a technical perspective the Loa product sets up an SMTP listener locally on your PC on port 25. It only accepts connections from localhost so it isn't creating an open relay of any sort. When you connect to it the app proxies your SMTP conversation to their servers in Canada via HTTPS over port 443. I've yet to run into a network where port 443 is blocked, so that gets around the port 25 risk. The server in Canada provides a standard SMTP conversation that any SMTP client can use/work with. From their server in Canada the message is then relayed using normal SMTP protocols to the appropriate MX servers and then on to the recipient. If you plan to make a habit of using them you should probably set up the correct SPF records in DNS for your domain so that they can be considered authoritative for your domain.

All in all it is a decent product for getting around the port 25 block. I was initially put off by the pricing, but even as a heavy user I doubt I'd surpass the $12/month plan (200/day, 100/month max). If you find yourself constantly stuck in situations where you're blocked from using regular port 25 traffic to send mail it is a pretty affordable solution that just works with truly minimal reconfiguration. They still have a few typos in the documentation (I've already given kgord a good ribbing on those :p) but the product does exactly what it advertises, which isn't such a bad thing.

My preference is to use an Exchange server with RPC over HTTPS for my clients, though I'm considering Google apps more and more these days, especially for the smaller ones. If you look at this porduct as SMTP over HTTPS similar to the way Exchange offers RPC over HTTPS you would see many parallels. The main difference is that they tunnel everything back to their environment rather than to your own. Otherwise it is pretty much the same concept.

S.

I routinely configure networks at my client sites to block all outbound port 25 traffic from any machine that isn't a known mail server that is supposed to be connecting to the Internet.That is, indeed, a standard practice.

However, most authenticated SMTP servers are (or should be) configured to also accept connections on an alternative port (typically 587 or 2525), and/or support secure (SSL) SMTP on port 465. For example:

Yahoo: smtp.mail.yahoo.com port 587, or SSL SMTP port 465
AOL: smtp.aol.com port 587, or SSL SMTP port 465
GMail: smtp.gmail.com port 587, or SSL SMTP port 465

Travellers, who are still connecting to their SMTP server on the default (and often blocked) port 25, should contact their ISP or network Admin to obtain those settings

Travellers, who are still connecting to their SMTP server on the default (and often blocked) port 25, should contact their ISP or network Admin to obtain those settings

Assuming the ISP offers it, this is obviously the best solution. Not every ISP does, so having alternatives is always a good thing.

I have to change my Outlook email setting to logon to server and check messages first and then it works for me

Assuming the ISP offers it, this is obviously the best solution. Not every ISP does, so having alternatives is always a good thing.Virtually every ISP offers it (since virtually every ISP blocks outgoing port 25 connections). Therefore, in most cases, workaround solutions like LoaPost are not really necessary.

I have to change my Outlook email setting to logon to server and check messages first and then it works for me
That is an issue with SMTP authentication for sending as implemented by your mail provider. If you can get that far then the network you are connecting on isn't the problem.
Virtually every ISP offers it (since virtually every ISP blocks outgoing port 25 connections). Therefore, in most cases, workaround solutions like LoaPost are not really necessary.
Like I said in my post, I don't use direct SMTP at all, so I don't know how prevalent the workarounds are. For major ISPs it probably won't be an issue. For someone running an in-house system in a small company it might be. And even if most ISPs (or at least the ISPs for most people, which is probably more likely) do offer port-based workarounds, there is no guarantee that those ports will be open (I have several clients who block everything but 80 and 443 from access for "regular" systems) nor is there a guarantee that everyone will be able to use them.

If one finds themself in a situation where there are not alternatives that can be managed for free and/or with configuration changes on their local client then alternatives might be needed. I expect that the number of situations where this would occur would be small, but better to know what the workaround is in advance rather than try to "discover" it in a pinch.

I am not advocating that anyone go out and buy a subscription immediately. But knowing that there is such an option out there and understanding how it works and what blocks it can evade is useful information.

That is, indeed, a standard practice.

However, most authenticated SMTP servers are (or should be) configured to also accept connections on an alternative port (typically 587 or 2525), and/or support secure (SSL) SMTP on port 465. For example:

Yahoo: smtp.mail.yahoo.com port 587, or SSL SMTP port 465
AOL: smtp.aol.com port 587, or SSL SMTP port 465
GMail: smtp.gmail.com port 587, or SSL SMTP port 465

Travellers, who are still connecting to their SMTP server on the default (and often blocked) port 25, should contact their ISP or network Admin to obtain those settingsArghhh, now I understand.

So all this time I've been sending and recieving emails without SSL ?!
No wonder I couldn't use my SMTP connection (port 25).
All resolved now though ^


...I suppose I have some comfort in that my wanted emails were well hidden amongst 90% SPAM.

My concern with sending e-mail from my own SMTP server is that my outgoing mail might get flagged as spam because the server doesn't match the domain of the mail. I use an Exchange server with ssh authentication and so far so good.

You can't have an IT director who wants to control the network running waht is essentially an open access network.

I'm in a Le Meridien right now, and they have Inter-Touch as their internet access provider. I wanted to send some e-mails, as many business travelers, I use Outlook for that. Once again, I have the problem that the access provider apparently blocks the SMTP port or something like that (I don't know if I am expressing that correctly - but the fact is that all the e-mails are stuck in my outbox).

This is annoying!!

What do these operators think? Isn't sending e-mails one of the things business travelers would do?? Why do they block this?

This is ridiculous.

What would you do, other than complain to the hotel and suggest they switch their provider?
I was struggling with the same problem, This is what I did and it worked. go into tools> Options>Mailsetup>Email Accounts>view change existing email accounts>change>more settings> -- click on Connection tab>Exchange over the internet option should have a check box selected>--click on Exchnage Proxy Settings>--under Proxy authentication settings drop down, slect NILM Authentication> Click OK, click next to complete and save the new Email Settings. Close Outlook and restart. Hopefully this should work for you too.

Try using outgoing mail port 587, many mail servers reply on this port and it bypasses common port 25 filters.

There are two separate mail protocols being discussed in this thread as if they were one. SMTP is the standard protocol for sending e-mail through POP. It uses Port 25. Most corporate setups using Outlook use an Exchange Server. Exchange Server's main port for mail is 135.


One solution that I've thought about posting before, but have mixed feelings about is Hotspot Shield. It installs a pretty good free VPN on your PC that gets you around a lot of the blocking problems. My hesitation in recommending the program is that I think it installs too much adware for the price. People have different budgets on this forum, but I'd rather pay $10 a month for a clean hosted VPN, but there are people who will think I am nuts and that they have better places for their $10.

What would you do, other than complain to the hotel and suggest they switch their provider?

Actually my "suggestion" to the manager would be somewhat different. :)

Woe be unto a hotel that provides me with internet service (especially one that is surcharged) and blocks me from using Outlook.

I am lucky, I suppose, that I haven't yet had this problem but I will not tolerate it if I do.

Think about it. They offer "internet service," not "restricted internet service."

Many ISPs block ports 135 and 139 as a security measure, since Windows networking runs on those ports and a lot of people have their computers wide open on those ports. Instead, ask your IT department about a HTTP exchange proxy. This is the commonly accepted way to set things up.