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If someone is unsure if he recited Tal UMatar, one has to repeat the Shemoneh 'Esreh (it's slightly more complicated, but let's keep it simple).

If one is unsure if he remembered to Bentch (recite Grace after Meals), one has to repeat it.

Just how unsure does one have to be for these and other examples?

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I would assume that any time one cannot answer definitively, that is a safek. Step 2 would use the decisor of chazaka to assume that he said it the way he has always said it until now (last known chazaka). –  YDK Jan 3 '12 at 21:02
    
I heard for the Tal Umatar example that if you if prayed Shemone Esre 90 times that you can rely that you have said it correctly. Also for Bentching it is Safek Deorayta and therefore as you may know- you must say it. However, this all falls under "Lo BaShamayim Hi- you didn't do anything even if you already said it. –  Hacham Gabriel Jan 4 '12 at 0:00
    
Also, I think this one of those "depends in which case." I don't think there is one Kelal for the idea of safek. –  Hacham Gabriel Jan 9 '12 at 1:07
    
There is a principle raised by the Mishna Berura (IIRC) when it comes to Hilchot Tefillin and the benediction recited over the tefillah shel rosh (ashkenazic practice to recite, but the recital is a safek since sefaradim do not recite it for whatever reason). After its recital (by ashkenazim), BSKML"V is recited. The reason for this is because the safek is not a complete safek (safek legamrei). I may be mistaken. Can't remember completely as it has been too long since I last refreshed my mind on this topic. Correct me if I am wrong, or notify me if I am right. Thanks! –  Adam Mosheh Jan 10 '12 at 21:23
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@Adam see comments here: judaism.stackexchange.com/q/13017/5 –  Seth J Jan 10 '12 at 21:50
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up vote 3 down vote accepted

When there is a doubt, we rule based on habits. If you've done X all the time for the past 30 days or so, we assume you are in the habit of doing it. If you are not, then we assume you forgot. The level of doubt required is very small, the slightest lack of kavana, is enough to cause a situation of doubt. However, in practice, since we assume (I'm not quite sure why) people always have a lack of kavana, it is left up to the person to decide if there is doubt or not.

Source is my shul rabbi who gave this same dvar Torah every time we made changes in the shemonah esrei.

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This is good. The question always pops into my mind when I feel like I might have said it but I really am not sure, so I go back and say it, and about 50% of the time I get a flashback that, in fact, I definitely did say it. Other times I don't get the flashback but still have the nagging feeling that I probably did say it, and I just feel I'm stuck in a Safek-induced Berachah LeVatalah. –  Seth J Jan 10 '12 at 16:38
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