Currently, according to a previous question on this site, we count the omer without doubt: "Today is the Xth day of the omer" because we have a fixed calendar, and because counting with doubt is invalid.
But what happened before the establishment of the fixed calendar? Did the community adjust their counting once the messenger of the new month arrived? Did Shavuot start on different days in different places? Did we count like we leyn on Sukkot chol hamoed ("Today is the 3rd day and today is the 4th day")? Or did folks in chu"l neglect this mitzvah?
Answer
According to the Dvar Avraham (1:34), the reason one does not count ספירת העומר מספק is because if you do not know for certain what number it is, that is not considered "counting" at all. According to this reason, if there was an actual doubt, you would not be able to count at all. As the Dvar Avraham explains,
אבל לפי דברינו הנ"ל נראה לומר דבר חדש דדוקא ביו"ט היו נוהגין אבותינו לעשות ב' ימים מספיקא, אבל בספירה באמת לא הי' אפשר כלל לאבותינו לספור שתי ספירות ביחד מספק לפי שזו אינה ספירה כלל כמ"ש ובמקום ובזמן שהיו מסופקין לא היה תקנה לדבר וצ"ל שלא היו סופרין כלל
I recently saw that R. Joseph B. Soloveitchik objected to the Dvar Avraham's position precisely because it is inconceivable that before there was a fixed calendar, Jews were unable to perform the mitzvah of sefirat ha-omer. This would have meant that generations of Babylonian Amoraim would not have been able to perform this mitzvah, which is not mentioned anywhere in the Talmud. (Quoted in R. Hershel Schachter's Nefesh HaRav.)
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