I have an experience that convinces me that it’s time for new Web server software.

Last week, I upgraded my office Internet connection from cable modem to DSL. The new connection has download speeds about 26 times faster than the old connection and it costs less than half the price. Upgrading was a no-brainer. The only thing I don’t understand is why it took me so long to realize that DSL was available in my area.

To upgrade to DSL, I had to lease or buy a DSL modem. Since it only cost $60 to buy, I bought it. I was very surprised to discover that it was also a wireless router. Within twenty minutes of the telephone man leaving, I had the wireless feature up and running and was connecting my network computers to it, thus cutting my Apple Airport Extreme Base Station out of the loop.

Things are never as easy as they seem — not that the configuration stuff seemed easy. It seemed hard. After all, I had to obtain a fixed IP address, then map it into the new router and use port forwarding configurations to point incoming traffic to my G4, which does server duty. If I talked about it in detail with a layman, his eyes would glaze over and he’d pass out. If I talked about it in detail with someone really knowledgeable, he’d know the truth: that I knew just enough about networking to make me dangerous.

I set everything up and, on Friday, had my DNS guy, Dave, make the changes to my DNS records. PGS Internet Services handles DNS for the 19 domain names I host in my office. In the past, I’ve handed over some of my more bothersome Web clients to them. PGS charges more than I do, but they have infinitely more patience. I think they feel like they owe me for the business, so they host my DNS for free. I try not to make changes, but this was a biggie and it had to be done.

By Saturday morning, the DNS had already propagated through to the Cable America DNS server. I access the Internet via wireless cable modem (how’s that for a contradiction in terms?) at home and I was able to connect to all of my Web sites except, for some reason, aneclecticmind.com. That came later in the day. Feedburner and Blogger still couldn’t see the sites, so I couldn’t update my podcasts or the ones I do for KBSZ. But I knew it was a matter of time.

By Sunday evening, everything was accessible from just about everywhere. Mission accomplished. Total downtime: less than the 48 hours I’d expected.

But, like I said, things weren’t as easy as they seemed. Because when I got to my office this morning, I quickly discovered that my production computer was unable to access my server for FTP, e-mail, or Web sites.

I had a lot of work to do — I’m still working on that QuickBooks book and I think I’m supposed to have it done by the end of the week. (Oops.) So I didn’t start troubleshooting right away. But it was driving me nuts that it wouldn’t work. And the fact that I could access it if I connected to the Internet via the Airport wireless network, which was still connected to the cable modem, was driving me nuts. So I went into full troubleshooting mode and spent about an hour banging away on it, trying all kinds of things, before I finally called the DSL modem company, Adaptec, convinced that it was a router configuration problem.

Now Adaptec has a technical support policy that basically says that they’ll help you with easy stuff for free but you have to pay $29 to get help with difficult stuff. Port forwarding for a shared static IP address fell into the difficult stuff category. But it was worth $29 to me to get it working right so I could stop thinking about it.

And that’s what I told the tech support guy I got on the toll-free phone number after about 10 minutes of waiting (their dime). But he said that he might not have to charge me. I should explain the problem.

So I did. And he knew immediately what the cause was. Here’s the simplified version. When you’re sitting at your computer and you type a domain name like www.aneclecticmind.com into your Web browser, your computer goes out to its DNS server on the Internet to find out the IP address for that domain name. In my case, it was learning that the IP address for the site I wanted to visit was the same IP address as the one I was trying to visit from. Adaptec routers don’t like that and they consider it an error so they don’t completely process the request. Apple Airport routers, on the other hand, are much more forgiving and let you visit yourself as often as you like. That’s why I didn’t get the error when I was using the Airport router and I started getting it when I began using the Adaptec router.

“How do I fix it?” I asked.

“You don’t,” he replied. “But there is a workaround. Just use the local IP address of the server computer.”

The local address is the address assigned by the DHCP services in the router, which I’ve manually set on the server computer. I typed that into my FTP software and it worked. Then I tried e-mail and it worked, too. Then I tried the Web browser and bzzzt. It didn’t work.

“It should,” he said. “There must be a configuration problem with your Web server software.”

Since I’d already taken up enough of his time and he’d solved most of my problem for free, I thanked him and hung up. The problem was sufficiently fixed to get my mind off it enough to work. I finished Chapter 6 of my book, then churned through 4 chapters of edits that had arrived that morning. I had to fiddle with my printer to get it to work on the network. I wasted about 30 minutes and 50 sheets of paper trying to get it to clear out a very old IP address so it would accept a new one from the router. No luck. But at least I could print.

Then I listened to my voicemail messages from the weekend, which I’d also put off until I was done working. By that time it was about 3:30, my normal quitting time. But instead of quitting, I dove into another troubleshooting session, this time with the folks at 4D.

4D, which started life as a database software company, bought StarNine, makers of WebSTAR Web server software, several years ago. I’d been using WebSTAR since version 3.0, when an evaluation copy of it had been given to me by Eric Zelenka, WebSTAR’s product manager. Back then I ran it under Mac OS 9 on an 8500/180 with an ISDN connection to the ‘Net. I believe Eric upgraded me to WebSTAR 4 and later I paid the big bucks to upgrade to WebSTAR 5. I’m currently running WebSTAR 5.3.3 on Mac OS X 10.3.9 on a 866MHz G4 with 384 MB of RAM.

Since upgrading to WebSTAR 5, all I’ve had is headaches with the software. The most bothersome thing is its spurious restarts: the software will shut down and restart itself about 100-200 times a day. For several months, I used 4D’s free technical support option — e-mail — to try to troubleshoot the problem. No luck. I gave up. I had to write an AppleScript that would automatically go into a specific folder where WebSTAR kept storing “backup” files it didn’t need every time it restarted itself. I discovered the buried files when I realized that something was eating up my disk space: by that time, there were over 12,000 of the damn files in the folder. Now the folder is cleared out every morning as part of the restart process.

So today, I wasn’t expecting much from 4D technical support. I knew whatever help I got was going to cost me. $40 was the going rate at 4D. But again, I thought it was worthwhile to get the problem resolved by talking to a real person.

I called and talked to a real person after being on hold (my dime) for about 15 minutes. To his credit, he really did try to help. But after going over the obvious — which I’d already done — he was out of suggestions. Time to “escalate” the case. That means time for me to break out my credit card.

He switched me to someone named David and he took my American Express card info. Then he tried to switch me back to the original guy. I was on hold for about 5 minutes when he got back on and told me the lines were busy and I’d have to wait in the queue. Duh. So I waited. My dime turned into a few bucks. On top of the $40 I’d already spent. At least the hold music was better than Adaptec’s.

Finally, a guy who sounded pretty French to me got on the phone. I groaned. Not because he was French, but because I knew I’d have to explain the problem all over again from scratch and he’d try all the things the first guy tried before getting down to real business. So I explained it. And he said, “I know exactly what the problem is.”

I laughed. “I bet you don’t. But I’m willing to listen.”

He spent the next 30 minutes crawling around inside my configuration files by accessing the server as an administrator. He made some small changes. He had me try accessing. It wouldn’t work. At one point, he had it set up so that I could use the local IP address to access one of my Web sites. But I wanted to be able to access all of them.

While he was fiddling around, I was thinking. Something he said gave me an idea.

“How about if we create a new Web site with a default folder that’s the same as the WebServer folder (the folder in which all of the other Web site folders reside). We can set that as the default that’s accessed with the local IP address. Then I can just type in a slash and the name of the folder containing the site I want. That should do it.”

“It won’t work,” he told me, dashing my hopes. He tried to explain why, but I didn’t really understand what he was saying.

I let him fiddle around for another five minutes. I was thinking hard. I couldn’t understand why my idea wouldn’t work. So I tried it. And it worked.

I told him and he had difficulty believing me. But it worked and although it wasn’t the perfect solution, it was a workaround I was willing to live with.

“So tell me something,” I said to him. “You didn’t fix the problem and I did. Do I get my $40 back?”

The answer, after a long story in which he explained that he was actually in charge of technical support, was no.

So I spent $40 plus about 90 minutes of long distance telephone time to come up with my own solution for the problem.

I’m still trying to decide whether I should call American Express and begin a chargeback for the $40. I didn’t, after all, get what I paid for. What do you think?

In the meantime, I’d spent a lot of that time on hold doing research. I discovered that Mac OS X 10.4 Server will indeed run on a G4. And it includes not only the well-respected and highly compatible Apache Web server, but e-mail, DNS, blogging software, streaming audio server, steaming video server, iChat server, and so many more things I don’t have. Of course, it is a bit pricey at $999.

But after my dismal technical support experiences with the 4D WebSTAR folks, I’m ready for a change.