What is the earliest time for the first cup for the start of the seder?
I would definitely follow the Gra (Biur HaGra on SA OH 261:2; MB ad. loc., no. 23) here and start as early as 14 minutes after sunset.
The only reason not to start earlier than tzeit is the Terumat HaDeshen (137) – then paskened by the Shulchan Aruch OC 472:1 – who holds that just as matzah can only be at (full) night, so too the arba kosot and all parts of the seder should be as well. That is a questionable extension, and regardless – everything besides Maggid and matzah are d’rabbanan and thereby more flexible. With this in mind, I see no problem relying on the Gra’s stance on tzeit to mark the beginning of the holiday, especially considering the other factors that are always at play (children needing to sleep, impatience, hunger, etc.). One should be makpid to not do critical parts of Maggid before normal tzeit. At the beginning of the seder, this would boil down to the 4 Questions (since Maggid is q&a) and the one sentence of עבדים היינו. Later on in the seder would include ארמי אובד אבי and more, but this is the part to focus on in the beginning.
Two other points regarding starting 14 minutes after sunset:
- You can do the 4 Questions before 45 minutes after sunset (and this usually takes a good amount of time), just as long as one is sure to do it again after 45 minutes (and you can skip all the singing, etc. in the repetition).
- Regarding if this can apply to the second night as well: The concern here would be that you say havdalah in this kiddush – המבדיל בן קודש לקודש, which might require more stringency in timing since it is marking the end of Shabbat. While I acknowledge these concerns, I still would allow starting after 14 minutes if it is felt to be important to do so. Technically speaking, when necessary (such as the tzorekh mitzvah of getting to the seder), havdalah can be said from plag ha’mincha on (without fire and with all the Shabbat restrictions still in place). Since this is already tzeit according to Gra, I would permit this kiddush at the start of the seder, even with the havdalah insertion. If this is done, it has to be very clear to everyone that you cannot make a fire, cook, or do any of the melakhot that are permitted on Yom Tov for the sake of food until 45 minutes have passed (no turning on the oven, putting uncooked food on the stove top, etc.). A step-by-step guide of this is listed below.
Setting the table for second Seder before tzeit (by any definition) in order to make kiddush at the tzeit of Gra is also not an issue. It is hachanah, which is a d’rabbanan concern, and one can violate actions that are categorized as d’rabbanan when they are l’tzorekh mitzvah during bein ha’shmashot. At worst it is bein hashmashot, and according to Gra it is technically night already!
Considering that you probably want the table set before making kiddush, you can start setting the table at shkiya – based on the principle above that d’rabbanans are allowed bein ha’shmashot l’tzorekh mitzvah (SA OC 342:1).
Happy Pesach prep!
Step-by-Step Guide: Shabbat leading into Yom Tov, starting seder earlier
- Set the table
- Feel free to reheat fully-cooked food that is not לח on a blech, warming plate, etc. (that is already on). You may even do this even directly from the fridge
- 14 minutes after shkiya – start seder
- Make kiddush with hadvallah (יקנה”ז), but do not light a fire, and do not do בורא מאורי האש (so it will be יקנה”ז)
- Do not do anything you can not do on Shabbat – cooking, lighting a flame, etc. – until 45 minutes after shkiya (or whatever is your normal tzeit)
- Once it is normal tzeit
- Light Yom Tov candles with a berakhah (להדליק נר של יום טוב) but without a שהחיינו, as that will already have been made at kiddush
- Make בורא מאורי האש on the Yom Tov candles
- Say Ma Nishtanah again if you’ve already said it earlier (this can be a single reading by one person without all the production)
- Continue from where you left off