Day 3 of trying to set up a VM for this legacy app. Demotivation is at an all-time high.

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    At least you're persistent. Keep it up 👍👍
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    I spent 3 days trying to figure out how to install a corporate build of Ubuntu on VMware. I spent a considerable time ambushing the only IT guy on site for passwords that were required for encrypting the virtual(!) disk, and all sorts of superuser privileges. I tried 4 different .iso till I got one that did not crush at some point during installation. Proxy issues by the pound.

    Just to figure out that the corporate configured the Sudo command to authenticate with a server an ocean apart, so it takes about 5-10 minutes to complete each time.

    I want to burn everything.
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    I feel your pain. Currently maintaining an intranet for a large bank and we're migrating to a new server this weekend. One query that worked OK in my Debian Jessie VM didn't work in production. In the end it turned out that the production server still ran MySQL 5.0, which I couldn't find packages for. Fortunately a move to a new server was imminent so this weekend we're moving it to MariaDB 10.2 and going from PHP 5.4 to 5.6.
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