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Are you allowed to put an envelope in your personal mailbox that will be picked up on Shabbos or Yom Tov?

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This question would be much improved if you'd indicate why you think it might be forbidden. – msh210 Apr 1 '12 at 18:57

I have never asked a posek, but I have done so since I do not specify a need for it to be picked up on Shabbos, and Sunday works just as well. The post office chooses their own time to pick up the mail (Its their preference to pick up on Saturday, not Sunday) so they are doing melacha on Shabbos for themselves.

Claiming that placing the mail there or raising the flag is similar to a command would mean I am not allowed to drop off my clothes at a launderer if I know for sure he's going to clean them on Shabbos, yet this restriction is not stipulated in the halachic sources.

I know of one rav who went into the post office on Friday to send an overnight letter (which would be a problem) and tried having a conversation with a confused postal worker about how he didn't want it delivered until Sunday!

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Can you order a pick up for Yom Tov? – Gershon Gold Oct 3 '10 at 3:01
I don't think so and probably not erev yom tov, either. When you place your mail outside, everyone knows you didn't ask the mailman to specifically deliver your mail on Shabbos. When the mailman does a special pick-up, that is similar to Shulchan Aruch 247:3. In that case, since there was a purchase of service on Fiday and all saw the mail guy start the service on Shabbos, it looks like the sender requested the service for Shabbos, despite his not caring when it gets delivered. – YDK Oct 3 '10 at 4:06

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