I wanted to run a Windows machine on my Mac OS X. So obvious choice was using WineHQ. Ideally, it should have been 1/ Download, 2/ Install and 3/ Run. However, it is never that simple, isn’t it!?

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macOS Catalina (10.15.1)
iMac (21.5-inch, Late 2102)

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1. I wanted to use HomeBrew, so I ran this command from https://brew.sh/ and downloaded needed components

2. I updated ~/vi .bash_profile and added

3. I downloaded version 5.3 from https://dl.winehq.org/wine/source/5.x/

4. Seems like this is a known bug https://bugs.winehq.org/show_bug.cgi?id=48689 and the fix has been provided here: https://source.winehq.org/git/wine.git/blobdiff/76606eaea034c51a73190aac92e75d8b20e82164.35c223850e1bc9e8f97bfaf403bfabca69db3447:/dlls/ntdll/locale.c

5. Edited wine-5.3/dlls/ntdll/locale.c accordingly (though the line numbers did not match)

6. Then I ran configure again successfully

Took a while, but was successful.

7. I fixed some X11 issues

8.Moment of truth:

9. I had to install more packages that WineHQ UI asks for a got few Mac OS X pop-up:

10. I went to System Preferences and allowed the executable by clicking “Allow Anyway”

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11. Finally, it worked.

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1. Downloaded WineHQ pkg for MacOS X from https://dl.winehq.org/wine-builds/macosx/download.html

2. It asked to me have the latest XQuartz installed. So I downloaded XQuartz 2.7.7 dmg from https://www.xquartz.org/releases/XQuartz-2.7.7.html. It installed successfully.

3. I tried reinstalling Wine again and it moved ahead this time. I chose 64-bit support (optional) while installing.

4. However, when I ran it from the Applications folder, I for an error that it needs to be updated and lead me to this page: https://support.apple.com/en-us/HT208436

Making WineHQ Work on MacOS Catalina

1. I wanted to use HomeBrew, so I ran this command from https://brew.sh/.

2. I followed instructions from https://wiki.winehq.org/MacOS/Building and downloaded version 5.3 from https://dl.winehq.org/wine/source/5.x/

3. I found this link and started following instructions: https://apple.stackexchange.com/questions/373851/how-to-get-wine-working-on-catalina. So I updated the command:

4. I wanted to use HomeBrew, so I ran this command from https://brew.sh/.

5. From https://stackoverflow.com/questions/10778905/why-does-my-mac-os-x-10-7-3-have-an-old-version-2-3-of-gnu-bison/30844621#30844621 I realised that Mac has older version and thus upgraded it.

6. I updated ~/vi .bash_profile and added

7. Opened a new window which had the path updated

8. I ran configure again successfully

Took a while, but was successful.

9. I had to fix some X11 links.

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10. Moment of truth

Whaaaaaa …….

11. Seems like this is a known bug https://bugs.winehq.org/show_bug.cgi?id=48689 and the fix has been provided here: https://source.winehq.org/git/wine.git/blobdiff/76606eaea034c51a73190aac92e75d8b20e82164.35c223850e1bc9e8f97bfaf403bfabca69db3447:/dlls/ntdll/locale.c

12. Edited wine-5.3/dlls/ntdll/locale.c accordingly (though the line numbers did not match), deleted locale.o and restarted

13. Phew! No Segmentation faults. However, there are more hurdles. After waiting for a while, I got 2 issues.

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14. I went to System Preferences and allowed the executable by clicking “Allow Anyway”

15. Then I installed FreeType using HomeBrew /portable-photoshop-cs5-for-mac-free-download.html.

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16. Tried again and had to repeat the step-14 multiple times for various DLLs. I had to export another env variable in ~/.bash_profile

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