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UPS Worldship 2019 under CrossOver 18.5

Hi everyone.

Trying to install the newest version of UPS Worldship, as an unlisted app, from the Worldship DVD.
As this version requires Windows 8 or newer for a clean install, create a Win 10 64bit bottle.
Get message that the app requires .NET framework 4.6.1. Proceed to attempt .NET install, which stalls out early on in the process and eventually throws up an error, which also causes the Worldship installer to fail since it can't find the necessary .NET framework.
Attempt to install the listed .NET framework 4.6.1 into the same bottle. This also grabs the dependencies, .NET framework 2.0, .NET framework 2.0 service pack 2, and .NET framework 4.0. .NET installer throws up errors on all of them except 4.6.1. Despite this, all show up as successfully installed in CrossOver.
Re-run Worldship installer on the same bottle. Installer does not recognize .NET framework 4.6.1 as installed, attempts to download and install 4.6.1 again, and hangs as before.

I'm trying with a clean Win 10 32bit bottle right now, and starting with the .NET frameworks first. While that's going on, is there anything I should have done instead of the above steps? I haven't used CrossOver in years, and am groping around in the dark here.

Update:
1) Clean install into a Win10 32bit bottle. Started with .NET 4.6.2, as it should be backwards compatible with 4.6.1. No error messages on any of the dependencies (.NET frameworks 2.0, 2.0 SP2, and 4.0), however the 4.6.2 installer displayed a success confirmation screen and hung, requiring a force quit of the pre-loader. Force quit aside, the install was successful.

2) Attempt to install Worldship 2019 from DVD into the same bottle. Installer launches successfully, but requires MDAC 2.8 SP1 or newer, and exits when one isn't detected.

3) Install MDAC 2.8 SP1 into the bottle. CrossOver does not recommend installing into anything newer than Windows XP, but the install was successful.

4) Re-run Worldship installer. Installer warns about recommending IE11 and only having IE9, but begins install process. Select standalone workstation install. Installer fails at step 4 of 26, unable to locate MS SQL server 2014 SMO (server management objects). I'm currently stuck here, as I can't figure out how to install just the SMO into the bottle, or whether that's even possible.

Regrettably, I'm admitting defeat. I tried to bypass some of the issues by downgrading to WorldShip 2018 and the OS to Windows 7 32bit. I got fewer errors during the .NET and dependency install, and got to step 5 in the WorldShip 2018 install before running into yet another MS SQL server error. I'm going to declare this a lesson for the future and go try a full-on VM.

For anyone else fighting with UPS software on a Mac, I recommend looking at NRG (nrgsoft.com). It's subscription-based and isn't exactly cheap, but it's pretty much the only option we've found so far that isn't a web-based solution.

CrossOver Forums: the place to discuss running Windows applications on Mac and Linux

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