Geek: VPN, email and hotel Wi-Fi

One of my colleagues has found emails go missing when travelling. We tracked it down to their hotel Wi-Fi provider being marked down for spam by the incoming mail server.

Now I expect we should be using VPN for all sorts of sensible security reasons, but does the house think it will get around this particular problem of email getting spamtrapped?

Finally, any specific recommendations? A mate of mine off here was kind enough to recommend http://www.anchorfree.com. Sound alright? My colleagues need something idiotproof, I’m the closest they’ve got to an IT Dept. Thanks!

*Incoming* mail server? What is it?

I can see how outbound might be a problem, but I’m not seeing how inbound would. For the purposes of spam filtering a server generally doesn’t care where mail’s going, only where it’s come from.

How did you ‘track it down’, can you explain the setup in a bit more (ie, any) detail? I may be missing something here but that doesn’t make a great deal of sense to me.

Stuff she’s sending out not being received by clients. Client’s IT: ‘oh yes, sunraytv are known spammers.’ Sunraytv supply Wi-Fi to lots of hotels in the US. Ta!

I thought we’d sorted this for you..

Anchorfree is one of the ones we see here quite a bit, seems fine.

My colleagues need something idiotproof, I’m the closest they’ve got to an IT Dept.

Oh dear.

Indeed Jon. Outed! I trust you implicitly but am scared to tell them what to do without the backing of the hive mind. As soon as I do that I become their technical support 🙂

oh yes, sunraytv are known spammers

Is she using sunraytv for her e-mail? If not, that’s totally irrelevant as the client’s mail server would have no way of telling that her e-mails were being sent via a sunraytv Wifi network. Her e-mails would first have to go via her own e-mail server, which won’t forward on a trace of the route by which they got there. That appears to be a total red herring (unless for some strange reason she does use a local mail server when travelling).

What e-mail provider is she using? Is it a corporate one, or her own personal one? If the latter, then I recommend switching to gmail – that uses https by default, meaning there it’s just as secure as using a VPN.

You suggest e-mails are going missing on the way to the client – can you check whether the mail server she is using shows them as having been sent. That would at least sort out whether it really is the client’s sever rejecting them, at which point you can check the exact content of what has been sent to see where the problem is – as mentioned above though, there really should be no trace of the hotel’s wifi in an e-mail.

Is she using sunraytv for her e-mail? If not, that’s totally irrelevant as the client’s mail server would have no way of telling that her e-mails were being sent via a sunraytv Wifi network.

This.

Use your email provider’s SMTP server for outbound mails. You will almost certainly need to use authentication and probably encryption – see your provider’s FAQs on how to do this.

Or, use webmail, which will have the Internet-based server as point of origin and bypass the problem completely.

That’s the nub of the problem. Our server (Dreamhost) shows them as sent without a problem. The incoming IT people mentioned this sunraytv thing. I was surprised that it showed up in the trace, but like I say know slightly more than nothing.

Fall back position was to use a gmail acocunt, which gets through fine as you hint, but not a great solution reputation/corporate standards-wise.

I’ll put them onto VPN because it’s the sensible thing to do, but I suppose I’m after reassurance that it will also solve these email problems.

Known problem for ‘old’ hotel Wi-Fi and/or ‘old’ Laptop SMTP setups where people did not have a ‘roaming’ style of setup

As Cougar says you would be better off making sure everyone is using the same SMTP server settings for all outgoing e-mail. Your e-mail providers settings will almost certainly work

VPN could be a bit overkill unless you need it for other reasons

It’s hard to tell whether you’re going to solve a problem when you’re yet to define it fully.

Ask for a copy of the email header from the recipient, that should help shed light onto what’s going on.

Is she using sunraytv for her e-mail? If not, that’s totally irrelevant as the client’s mail server would have no way of telling that her e-mails were being sent via a sunraytv Wifi network. Her e-mails would first have to go via her own e-mail server, which won’t forward on a trace of the route by which they got there. That appears to be a total red herring (unless for some strange reason she does use a local mail server when travelling).

Not true – Looked at any email headers recently? Pretty much all except gmail messages have the IP address of the sending computer (not the server) in the headers. Pretty standard to do that.

So that is why non-gmail webmail is not a solution, but gmail is.

VPN should fix it.

Use your email provider’s SMTP server for outbound mails

This still will have hotel Wifi IP address as the originating IP, and that may be what is blacklisted and triggering spam detection somewhere.

Or, use webmail, which will have the Internet-based server as point of origin

May also have hotel Wifi IP addy as one of the originating IP fields.

Need to use VPN or ssh tunnel or something to get around that.

As Cougar says you would be better off making sure everyone is using the same SMTP server settings for all outgoing e-mail. Your e-mail providers settings will almost certainly work

Won’t fix it. Sending IP address still in the headers.

Remind me, are they using a native email client or webmail? Webmail clients will quite often stick the actual source ip address or name to the email headers which may be cause an issue here.

A VPN is the right thing to do anyway. Passing potentially sensitive corporate emails over an open hotel wifi system is a method waiting to fail.

It sounds like the incoming mail people aren;t giving you an absolute answer on why the emails are being blocked, which is a bit poor. I’d want a definitive answer from them on what the cause is before providing any assurances that this will resolve the issue.

I’d want a definitive answer from them on what the cause is before providing any assurances that this will resolve the issue.

Bingo.

IMLE hotels ‘systems’ get blocked because of the Mail server settings, not the IP address that originated them, but that’s not to say it is definitely whats going wrong here.

As above more info required

Looked at any email headers recently?

Only gmail ones 😳

A VPN is the right thing to do anyway. Passing potentially sensitive corporate emails over an open hotel wifi system is a method waiting to fail.

This. Hence the recommendation for gmail which doesn’t have an issue with passing unencrypted stuff over wifi. Personally I’m always very wary about what I do over any public wifi, even if it does have some encryption.

It sounds like the incoming mail people aren;t giving you an absolute answer on why the emails are being blocked, which is a bit poor.

Though looking at the full contents (including all headers) of what your server has sent out might give you a clue.

VPN can fail if the hotel wi-fi will not allow pass-through, or support the protocol you are using. Anyone with a Virgin SuperHub using L2TP will be familiar with this (I have to turn of the hub firewall to access work, a fix is coming mid-May so the tech chap said).
I would be very wary of entrusting anything commercially sensitive (or possibly sensitive) to a US based company. Echelon is used for business espionage too!
Oh god, a knock at the door.
Orange one piece is not my thing thanks……