Submitting this because I dont have the time (or resources) to debug this atm and need a self-reminder:
On Win32 walletpassphrase does not appear to relock after the designated amount of time as it should and as it does on Linux.
Can someone check this on OSX as well?

key.pushKV("scriptPubKey", HexStr(GetScriptForRawPubKey(coinbaseKey.GetPubKey())));
        key.pushKV("timestamp", 0);
        key.pushKV("internal", UniValue(true));
        keys.push_back(key);
        key.clear();
        key.setObject();
        CKey futureKey;
        futureKey.MakeNewKey(true);
        key.pushKV("scriptPubKey", HexStr(GetScriptForRawPubKey(futureKey.GetPubKey())));
        key.pushKV("timestamp", newTip->GetBlockTimeMax() + TIMESTAMP_WINDOW + 1);
        key.pushKV("internal", UniValue(true));
        keys.push_back(key);
        JSONRPCRequest request;
        request.context = &context;
        request.params.setArray();
        request.params.push_back(keys);
        UniValue response = importmulti().HandleRequest(request);
        BOOST_CHECK_EQUAL(response.write(),
            strprintf("[{\"success\":false,\"error\":{\"code\":-1,\"message\":\"Rescan failed for key with creation "
                      "timestamp %d. There was an error reading a block from time %d, which is after or within %d "
                      "seconds of key creation, and could contain transactions pertaining to the key. As a result, "
                      "transactions and coins using this key may not appear in the wallet. This error could be caused "
                      "by pruning or data corruption (see bitcoind log for details) and could be dealt with by "
                      "downloading and rescanning the relevant blocks (see -reindex option and rescanblockchain "
                      "RPC).\"}},{\"success\":true}]",
                              0, oldTip->GetBlockTimeMax(), TIMESTAMP_WINDOW));
        RemoveWallet(context, wallet,  std::nullopt);
    }
}
BOOST_FIXTURE_TEST_CASE(importwallet_rescan, TestChain100Setup)