I am unable to get you the exact request that fails or a code snippet at this time as I am currently working on another project but I can tell you it is the very first request DownloadPreplannedOfflineMap makes once started (a /data endpoint if I recall correctly). We have a challenge handler set but it doesn't get called at all when this happens. The request/download task simply fails with a 498 HttpRequestException. We get the 498 after we start DownloadPreplannedOfflineMap. By the time we get to this point, other code has already run that is using security successfully. But if the download is started after the token expires (if the app was sitting open for a while) we get the 498. If we do pretty much anything else, like re-create the preplanned map area object before we download, that will successfully refresh the token. Sometimes the refresh happens transparently by the runtime, sometimes it uses our configured challenge handler (we haven't figured out what the determining factor is that chooses which to use) and the download will occur successfully if tried after.
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I am experiencing this same issue, and am able to reproduce it with Version 100.5. Attached is a zip file with a small reproduction app (the app also demonstrates a separate issue with an Access Violation Exception which causes a crash, hence the App's name). I've also emailed the support team about both issues. Update: I just tried one of the Xamarin Forms sample apps ("Display Device Location") and was able to reproduce the issue there.
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