Hi @Emmett Carey ,
Is your user on a VPN within a trusted network? The VPN could be disconnecting and dropping to the user's own ISP IP, which may trigger the MFA. If you check the browser logs you may be able to get more hints.
Since the same conditional access policy is being applied and the MFA requirement shows "previously satisfied", it's possible that the PRT with an MFA claim has been used. This could be legitimate, or the account could be getting flagged for a token theft issue. Do you see anything suspicious on the account logs?
Since it's hard to know for certain without seeing your specific policies, feel free to reach out to me at AzCommunity@microsoft.com ("Attn: Marilee Turscak") and include your subscription ID and a link to this thread, and I will gladly enable a support case for you to look into this scenario.
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