Illustrator last 4 updates always stuck at launch

Since you have an Intel based Mac make sure that the latest version of Apple’s Rosetta 2 translation layer is installed on your iMac. This app is what Apple uses to run current programs on older Macs like yours.

Hi ​@Ebnograph ,

Thanks for reaching out and sorry to hear that you're experiencing this issue. Could you please confirm the exact Illustrator version you're using? You can check this in the Creative Cloud Desktop app under the Apps tab.

I would also recommend manually backing up and resetting your Illustrator preferences, then testing whether Illustrator launches normally afterward. You can find the steps, along with a video at the bottom of the article, here:
https://helpx.adobe.com/illustrator/kb/troubleshoot-preference-issues.html

If the issue persists, please try the troubleshooting steps outlined in the following article:
https://helpx.adobe.com/in/illustrator/kb/fix-crash-on-launch-issues.html

Additionally, if the issue continues, please create a new macOS user account and test launching Illustrator from there. This will help us determine whether the behavior is related to your current user profile or is system-wide.
Ref: https://support.apple.com/en-in/guide/mac-help/mh15191/mac

Please let us know the results after trying these steps, and we'll be happy to investigate further.

Looking forward to your update.

Thanks,
Abhishek