"I've got this too" (sorry) but did want to add supplemental information: the stuff Jeff says on the radio seems correct. He talks about rain letting up, getting heavier, etc, and the need to switch to intermediate/wet etc in response. That is to say, the virtual crew properly recognizes the changed circumstance, the problem is specific to the MFD interface's new strategy.
More formally:
1. DESCRIPTION: Known issue of, when weather changes, two problems arise: (a) the MFD prompts a new strategy, but the only strategies are keep current & track update (b) unless the player specifically selects the the type of new tires, the tires will not be appropriate for weather, e.g., rain will start, every other car switches to intermediates, and the pit automatically gives you medium compound slicks. However, on the radio Jeff appears to provide accurate information about the need to switch tires, so the problem is specific to the MFD interface's new strategy.
2. SYSTEM: PS4 Pro
3. VERSION: Unsure, but is latest update to PS4 as of July 17, 2020
4. MODE: Career My Team
5. REPLICATION: Have observed 5 times, including twice on the same race (Zandvoort, quit without saving, raced again, rain came in and same problem arose). I can't 'replicate' because AFAIK I can't create new weather mid-race, but that's how you'd replicate: start a race with no expected rain and a dry strategy, then have rain come in. New MFD strategy will be prompted, but there will be no actual new strategy, and pit-stop will continue to give dry weather tires specified by the pre-race strategy.
6. TROUBLESHOOTING: The 'troubleshooting' is for me to select tires myself then box this lap. This works, but is not ideal.
7. CONTROLS: Not related to controls.
8. DOCUMENTATION: N/A, identified problem.