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I'm designing a web app where you can download a single file or a dynamically-generated zip file of several files.

For single files, I am planning for the file to be downloaded immediately.

For multiple files, there may be a long delay before the zip file is generated so I am providing a busy indicator. After the zip is ready, the download is automatically triggered.

I am considering providing a message here that says "Your download will start shortly. If it does not start automatically, click here."

Is this necessary?

I know apps like Dropbox don't offer this, but they might be catering for more savvy users who know that they need to disable download blockers etc.

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Issues with automatic downloads are often something that the person trying to download can't do anything about. Often corporations, universities, and schools disable many setting in browsers as part of their security settings, and an individual user has no way of changing those settings.

So, if your web app is likely to be used in any environments like that, I would suggest having an "if your download doesn't start ..." link to trigger the download.

That said, if you're preparing the downloads and that takes time, you should communicate this to your users. There are many options such as: "Preparing your files for download" or "processing your request" that can be used here, just choose something that is clear for your users. I wold also suggest some sort working animation to show that something is still happening should be shown with it such as a spinner or a progress bar (if you can get the intermediate information needed for that).

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Yes. In fact, I would even word it as (in the case of a multi-file zip) "Preparing your files for download...". This tells the user why they have to wait, rather than just saying "shortly" which the users don't know how long that would be. If it's not too technically difficult, providing deterministic progress is always the ideal.

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