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Masechet Shabbat says that when you give the benefit of the doubt, Hashem will give you benefit of the doubt. However, Hashem cannot have the benefit of the doubt. The benefit of the doubt relies on Hashem has doubt. But HaShem has no doubt! So how can HaShem have the benefit of the doubt?

Shabbat 127b ת״ר הָדֵן חֲבֵירוֹ לְכַף זְכוּת דָּנִין אוֹתוֹ לִזְכוּת

Our Rabbis taught in a baraisa: in a baraisa: in a baraisa: One who judges his friend on the cup of merit, they judge him favorably in Heaven.

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    The quote you bring only says that one who judges his fellow favorably, is [accordingly] judged favorably. Where is doubt mentioned? – Tamir Evan Apr 16 at 2:30
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1) The Baal Shem Tov explains based on the Mishna Avos (3:16)

וְנִפְרָעִין מִן הָאָדָם מִדַּעְתּוֹ וְשֶׁלֹּא מִדַּעְתּוֹ, וְיֵשׁ לָהֶם עַל מַה שֶּׁיִּסְמֹכוּ, וְהַדִּין דִּין אֱמֶת - they exact payment from man, either with his consent or without his consent, and they have that on which they [can] rely [in their claims], seeing that the judgment is a righteous judgment

that we are judged in the Heavenly Tribunal the same way that we judge others. For instance, if we see someone running late into shul, we can think about how they're lazy, unorganized, and don't care about prayer, or consider that he has many challenges in his life which he is valiantly trying to balance and it's amazing that he finds some time to pray with a minyan.

When the same scene is played in your video biography in Heaven as you run into shul late, they judge you however you did your fellow man.

2) Alternatively, the Ben Ish Chai (Shabbos 127b) asks your very question and offers the following:

יש להקשות דבר זה שייך לאומרו לגבי אדם שאינו יודע הנסתרות, אך הקב"ה יודע האמת וליכא ספיקא קמי שמייא, ואם יש לו זכות בודאי יזכהו ואין צריך לזה בקשה ותפלה? ונראה לי בס"ד דבקשה זו שייכה בכהאי גוונא כגון שהוא לא נתן צדקה כי היה עני, ומבקש שידין אותו הקב"ה לכף זכות לחשיב לו כאלו נתן צדקה, שיאמר אם יש לו היה נותן, וכן אם נחלה ולא התפלל, ולא קיים מצוה פלונית, שידונו לכף זכות שאם לא היה חולה היה מתפלל ועוסק בתורה ומקיים מצות. אבל אין הכונה לומר היכא דעשה מעשה שיש להסתפק בה אם כונתו לרעה או לטובה, דזה ודאי קמיה שמייא גלייא וליכא ספיקא, וכפי האמת ידון אותו, ולא שייך על זה בקשה ותפלה - If a person has no money with which to give tzedakah and asks Hashem to judge him as if he gave charity, or got sick and couldn't accomplish certain Mitzvos and asks Hashem to judge him as if he did the Mitzvos because that's what he really wanted to achieve, then Hashem may favorably look upon your situation to see how you acted when you had a little money to spare or were healthy enough to do Mitzvos.

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