Unable to access certain websites using SSL over Qwest DSL circuit using PPPOE

We recently had a Qwest DSL installation for one of our small business clients turn in to a bit of a nightmare.

After the circuit was installed, the client reported that they weren’t able to log on to several websites, including their QuickBooks Online account and Hotmail. After some initial diagnosis, it became clear that there was a problem accessing websites over an SSL connection—though not all sites were affected.

Given the presentation of this issue, we spent a few frustrating hours checking and rechecking the firewall (thinking there was something wrong with NAT—since some of these sites were accessible directly from the server), the internal DNS server (since Firefox would eventually return a DNS error after logging on to these sites), and the machine certificates (thinking that the workstation’s list of trusted certificate authorities had somehow become corrupt).

We were fairly confident that the DSL connection itself wasn’t involved because these sites were accessible from the server and from our own machines when we connected to the client’s network using a VPN connection and routed our internet traffic through the client’s default gateway.

We finally contacted Qwest to double-check the configuration of the Actiontec ADSL modem they provided. The technician with whom we were connected let us know that they had observed a very rare issue with their DSL service which was preventing a small number of their customers from accessing certain websites using SSL—not all sites, just a few.

Apparently, the problem is related to the use of the PPPOE on some of their DSL circuit and the only reason, it seemed, that Qwest was even aware of this issue was because MSN (which they often include with their residential DSL packages) was one of the affected site. Once we changed the protocol from PPPOE to PPPOA, the problem was resolved.

Unfortunately, this particular client had recently suffered through a series of technology-related misfortunes, including a blunder by Clearwire, so I was hesitant to go back to them with what might be perceived a work of IT-fiction.

You know what I’m talking about—that incredibly rare, technically-dense issue that they just happened to have the misfortune of experiencing which required several hours of billable time, and which they are in absolutely no position to know whether or not they’re being taken for a ride. I hate these kinds of issues—the ones where our clients end up shrugging their shoulders and relying on the trust and relationship we’ve built.

The good news was that the Qwest technician was polite enough to stay on the line, while I conferenced in our client, and explain what had happened.

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