Hello, I'm having an issue with Windows Chicago/95 build 58s.

So, I install MS-DOS 6.22 and CD drivers with no issues, then installing Build 58s using DOSSETUP.BAT, I'm able to get through the first part of setup, but after it restarts and gets past the boot screen, I get stuck with a frozen cursor. I've also tried a MS-DOS 6.22 boot diskette, but still nothing.

I'm using VMware on Windows 10 with these VM specs:
16 MB RAM
8GB HDD

This is pretty ridiculous, and I've had it work it the past. I downloaded Build 58s it from the BA FTP.

Use PCem for such early Chicago builds.
PCem is very complicated, so you may have to look for a tutorial,
Also I suggest you use MS-DOS 6.0, as that was the latest DOS version at the time of build 58s's release.
Use 2GB of hard drive space instead of 8GB.

I've tried PCem many many many times in the past, and it never works, ever. I've tried like 10 to 20 times, and spent hours on it, but I can never get it to work, so I gave up on it a few years ago, and I refuse to touch it ever again. A virtual PC should be simple. It should give you easy to use options that work. PCem is a broken mess that doesn't work. And yes, I've looked up several tutorials and lessons.

I would use VPC2007, which I know works, but it doesn't work on Windows 10. I've successfully installed Windows 95, and Windows 3.1 on VMWare with little to no issue.

Then check if you have an older computer that has Windows 8.1 or prior so you can use VPC 2007.

Go for 1 GB... This is the safest option for anything below 4.00.122.

Win7

The only other computer I can use right now is best suited for Windows 2000 or earlier, but I'd prefer not installing the OS on that.

86Box didn't even exist a few years ago, it changed a lot.

No such issues here on 86Box, and VMware is strongly inappropriate for running such Chicago builds like this.

Excuse me, if this sounds a bit rude: As explained many times before on this forum, you're using the wrong tool for the job. You said in a reply that you wouldn't use the build on a computer that's best suited for Windows 2000 - why are you using it on a computer that's much newer (which is essentially what you're doing with VMware)? You can't expect it to work flawlessly and you really shouldn't complain if it doesn't.

Lastly, 16 MB and 8 GB HDD is way too overkill for a theoretical machine designed to run Windows 3.1. 75% percent of your disk is most likely unallocated! FAT16 maxes out at 2 GB partition size. 4 MB and 1 GB HDD would be a much appropriate configuration and even that is probably too much hard disk space for such an early version of Windows.

A 486 processor, 4MB of RAM, generic VGA, 1-2GB hard drive partitioned and formatted with DOS 6.x and an ATAPI CD-ROM used with MSCDEX or a SCSI CD-ROM should be a working config. I've used something along these lines myself and had no issues.

When I did my emulation of Chicago 58s, I managed to get it to work on PCem on a Pentium with 256MB RAM, VGA (S3 VIRGE didn’t work), and MS-DOS 6.22 with 500MB hard drive. However, such thing is still overkill for something this early so I do recommend using the same specs as Windows for Workgroups 3.11 too. Using VirtualBox or VMWare for DOS Windows or Windows 9x is highly not recommended.

That are you say, @BF10. I habe 75 Virtual machines with Windows 95 Betas, and 58s is one of them and it have Cd-Rom Driver too. Just Klick in my signature the Link, JimOlive.

If you use PCem or 86-Box, use a 386/486, 64MB of RAM, and 250MB of disk space. I've installed it on VirtualBox, but it was NOT easy. Windows 95 on VirtualBox in general is not appropriate for the era of OSes. On VMware it is worse. In VirtualBox you need to turn off the VT-x/AMD-RV. I would use 86-Box or PCem.

What's the point of using 64 MB of RAM for an operating system that was designed to run with at least 4-16 MB of memory? Especially for such early betas that can be quite picky when it comes to hardware configurations...

Today actually (happy New Years!) I installed Chicago 58s and despite a krnl32 error it seems to run perfectly on vmware fusion 8 although I can't really install any drivers

Or you can take my Machine, Link is in the Signature, it works perfect without problems and it have CD-ROM Driver too because i did install it in VMWare 12 Pro and it works perfect on Version 14.1.1

It's my default configuration for Windows 95 builds. It works perfectly, and so I have no complaints.

What configuration you used (Machine type and other)?