What would signal would Harry think best? Something you could detect at the time of signalling, like a broken toothpick in your pocket, or a signal detectable safely in the future, like a penmark on the inside of your pocket? Probably both.
A rememberall.
Surely this would also be a relatively high priority for his research too. In fact Harry explicitly made a note to himself to research mental magic near the top of his todo list. That should have turned up a device or spell that detects obliviations and he should be in the habit of using it on himself regularly. Which reminds me about the research he is supposedly doing. What has he discovered? What useful spells has he learned? He's supposed to be a genius of near-Hermione level academic skill and far more strategic thought. When are we going to start seeing him pull out awesome, practical magical knowledge or skill?
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But we know Hermione didn't send herself a signal. Anything simple and quick enough to do unobtrusively (like biting her lip) would have been instantly noticeable to her on the second iteration.
We know Hermione didn't send herself a signal she could notice instantly on a second iteration. As of ch76, we do not know if she sent herself a signal not instantly noticable.
You might not want to use a signal that could be detected by yourself during an obliviation event in order to make sure the signal isn't telegraphed to the obliviator.
Harry might think that if one needed to signal obliviation, it might be best to detect it safely in the future, unless he thought he could make use of an instantly detectable signal and a tactical response would be worth risking interception. In Ch. 6 he risked interception of the signal (he told the potential obliviator McGonnagal about it) in order to forestall obliviation. I doubt that that tactic would work with Mr. Hat and Cloak/Ms. Veil/...