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I am using Delphi 13 with version 16.2.1 and entering a CSS file name in the content files string list. When I modify my CSS file and restart the program, it looks like the CSS file is not reloaded as it still has all my old code. I have to rename my file and re-enter the name in order for the changes to take effect.
Also a general FYI- TMS has discontinued their support for their Intraweb controls as of Delphi 12. This is the reason I had to add some CSS files with a small amount of code in them to do the same things using the standard Intraweb controls- removed their check list boxes and grids mostly.
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Ideally you should clear the browser cache. Browsers will cache content like external CSS files even if their timestamp has changed (the browsers actually won't check for updates unless some time has passed).
You can also use TIWServerInternalFiles to handle these files for you. TIWServerInternalFiles uses a clever hashing mechanism to always deliver the most up to date version available of the JavaScript or CSS file. If you are insterested I can point you an example
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It sounds like IntraWeb is caching the CSS file, which is why renaming it forces the server to pick up your latest changes. To avoid this annoying workaround while migrating away from those discontinued TMS controls, you might want to check if there is a caching property in your ServerController that you can disable during development.
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Man, TMS officially dropping their IW components in Delphi 12 was a huge headache for a lot of legacy projects. I had to migrate a massive app recently and had the exact same struggle replacing the TTIWAdvWebGrid. It's painful at first, but honestly, dropping the heavy 3rd-party components and just using standard IntraWeb controls styled with pure CSS or Bootstrap makes the final app run significantly faster and lighter on the DOM. You're definitely on the right track