2,421. "Put It on My Tab"
Maachalos Assuros 13:25
Let’s say that a Jew gives a dinar (a denomination of coin) to a non-Jewish shopkeeper. The Jew then tells his non-Jewish employee to go eat and drink on his tab and he’ll settle things with the shopkeeper. In such a case, he must be concerned that the employee will drink wine because this would be like buying libation wine and giving it to him. Such arrangements are also prohibited vis-à-vis the Sabbatical year. Let’s say that a Jew gives a dinar to a Jewish shopkeeper who is a layman. He tells his Jewish employee to eat and drink on his tab and he’ll settle things with the storekeeper. If the worker eats untithed food, it is prohibited.
Maachalos Assuros 13:26
Let’s say, however, that the Jew told them to eat and drink the value of the dinar that he already gave the shopkeeper, or just “Eat and drink from the shopkeeper on my tab and I’ll pay.” In such a case it is permitted because, even though the Jew is obligated to pay, his obligation isn’t directly tied to what the employee eats. In such a case, he needn’t be concerned about libation wine, Sabbatical produce or tithes.