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You're a freelancer. A client of yours finally pays a bill — seven months late! — via email money transfer.

Should you send him a thank-you email? Or should you simply be silent?

And why?

(We acknowledge when someone's done something for us. We even acknowledge inanimate objects for their contributions: e.g. Moses didn't strike the land since it'd hid the Egyptian for him. But I don't know how far hakarat ha'tov goes. Does it extend to cases where someone's inconvenienced you, or when you may inadvertently be training him that wrong behavior is okay?)

Please cite sources if possible.

Dear readers: CYLOR.

P.S. If you do future work for this client, perhaps you should insist on full payment in advance.

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Dear @YEZ: thank you very much for your edits. –  unforgettableid Mar 17 at 23:27

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It seems that the Torah puts two separate obligations on you – hakarat ha'tov and tochacha (rebuke).

You owe your Client some thanks because he could have tried to avoid paying altogether or caused you more costs in recovering the debt.

For this attitude, see here -a small quote:

“Moshe gets to the well. The daughters of Midyan are in trouble and Moshe saves them. They thank him. He says don’t thank me, thank the Egyptian. Listen I don’t deserve all the credit, I killed the Egyptian that’s why I'm here. Thank the Egyptian”.

The event is in Shmos 2 (17 - 19) and the Egyptian is mentioned in Shmos 2 (11- 12).

For the details of the mitzva of tochacha including when it can and cannot be done see Halachipedia.

I would suggest that both the thanks and the tochacha should be done sincerely

"privately and gently"

in person or, if not possible, by phone.

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