Windows 95 was a game changer, especially for Internet connectivity. The built-in "dial up networking" / PPP was huge. I was working at an ISP at the time, and remember how difficult it was to get customers to download Trumpet winsock and set it up for Windows 3.x. It could take hours with a difficult customer.
I worked at an ISP in 1997 (the “You’ve got mail” one) and thankfully the software included a winsock. Our headaches were different; They had just come out with unlimited hours and busy signals were the cause of many complaints. After that got resolved, custom modem strings were really the only complicated bits.
I recall the original Windows 95 release shipping with TCP/IP but the protocol having to be manually added in the Network CPL: https://eml.berkeley.edu/wp/win95/isp.html
Yes! This was still much easier than talking someone through downloading a Trumpet Winsock Zip with a comm program.
I did support for a tiny ISP in 1999 [1], we had to have people remove and reinstall that from time to time. Many people could just do it, but I remember one customer I spent maybe two hours on the phone walking her through it. Would put her on hold when another call came in, and then check back with her. Eventually got it all settled.
[1] we had one T1 for internet and one T1 PRI for the modem pool, and outsourced to MegaPath for out of area dialup, and then shunted all the customers to that when the PRI stopped working
This ISP was a bit earlier. They did move to T1 PRI eventually, but before that we had stacks of modems attached to Livingston Portmasters (I think?) There was basically an octopus of cables coming out of the wall, dozens of individual phone lines, then serial cables, power bricks, power strips three layers deep. It was also always like 100 degrees on one of the POPs. It looked like the plastic was melting on some of the modems.
Ow wow, worked ISP support in 1997 - 1999 and indeed recalled having to reinstall TCP/IP stack and tweaking setting to make stuff work. Next to that, gruesome installation of ISDN drivers (which technically were out of support for us) for a specific brand of ISDN modems the incumbent telco provided to customers.