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7. Squeezing juice out of pickles and other foods saturated with external liquids:
A. Squeezing out the liquid for the sake of drinking their liquids:
Fruits and vegetables that are pickled in salt and vinegar, or in salt water, as well as those which are cooked, are forbidden according to all opinions to be squeezed for their liquids.
The above is only a Rabbinical prohibition: If one [transgressed and] squeezed [the above foods] for their liquids he is not Biblically liable because even though the liquids were fully fledged liquids prior to becoming absorbed into the [foods], such as [occurs] if one pickled or cooked them in water or wine and vinegar and the like of other liquids, nevertheless since now they are being squeezed from food they have the same status as food and it is thus like separating food from food. Nevertheless, it is Rabbinically forbidden to squeeze them for the sake of their liquid since they were fully fledged liquids prior to this. However, raw fruits [that are not commonly squeezed to drink their juice] since their squeezed liquids never had upon them the status of liquids [prior to the squeezing] therefore it is allowed to squeeze them according to those opinions which permit doing so.
Squeezing fish: One who [wishes to] squeeze fish for its gravy has the same laws as squeezing pickled and cooked [foods] for the sake of their juices which is forbidden. [Some Poskim however learn this only applies towards pickled or cooked fish, however the natural gravy of the fish may be squeezed out even to drink, just as is the law regarding other fruits.]
May juice which had been directly squeezed into a food be then squeezed out of that food?
· For example: One squeezed lemon juice into his fruit salad and then desires to squeeze it out after it having absorbed the taste?
This is allowed to be done as since the juice which was squeezed into it never received a liquid status it therefore does not receive the same status as pickles and the like which contain juice that was previously defined as liquid. Nevertheless, it is proper to only rely on this in a time of need. [Vetzaruch Iyun Gadol as it is forbidden to squeeze the natural juices of the fruits in the salad, irrelevant of the juice it absorbed!]
B. Squeezing out the liquid for the sake of enhancing the food being squeezed:
One is allowed to squeeze pickles and the like for their own need, in order to prepare them to be eaten through doing this, [such as to making it taste better through doing so].
When squeezing out liquid in order to enhance the food may one squeeze the liquid into an empty vessel and then drink it?
The Poskim rule one may squeeze the liquid even into an empty vessel. Furthermore, some Poskim rule that according to this opinion one may even later decide to drink it. Others rule it is forbidden to drink the liquid. Furthermore, it is implied according to this opinion that it is forbidden to even squeeze the juice into an empty vessel and it must rather go directly to waste. From Admur here it is implied like this latter opinion that one may not drink the liquid and also must squeeze it in a way it goes directly to waste and not into an empty vessel, even if one plans to later throw it out. Practically, one is not even to squeeze the liquid into a plate but rather he is to squeeze it in an area that it will go directly to waste.
Why does squeezing liquid out from a food not contain the Borer/separating prohibition?
As the food and liquid that is absorbed in it are considered one food to which the separating restrictions do not apply as explained in The Laws of Borer Chapter 1.
If a food will only become edible due the squeezing may it nevertheless be squeezed?
No, as this poses a Borer prohibition. This may not be done in any cases, whether with intent to squeeze the liquid into food or to sweeten it.
May one squeeze liquid out from his challah if it fell into liquid?
Seemingly, yes as it is in order to enhance the food.
Practically, may one squeeze out the oil from a Sufganiya/Latke?
If he is doing so in order to enhance the food and make it more edible, then it is allowed. This includes if he is doing so due to that the oil absorbed in the food bothers him. However if one desires to use the liquid for other purposes then it is forbidden. As well to do so for no reason at all is to be avoided, as explained above. Squeeze directly into waist.
If one is doing so in order to both enhance the food and reuse the liquid, then see above Q&A where this matter is disputed, with the Tzemach Tzedek ruling that it is forbidden.
May one squeeze out the oil from eggplant or vinegar from cucumber salad?
Has the same laws as squeezing oil from Sufganiyot, as explained above.
May one squeeze out the juice of a fruit for no need at all but rather simply out of habit or the like?
See Halacha 2 Q&A there
C. Squeezing cooked and pickled foods into food:
It is permitted to squeeze pickled and cooked [foods] for the sake of their liquids into a pot of food in order to enhance the food.
If the pot is empty: However if the pot does not yet have food in it then it is forbidden to squeeze into it even though one will eventually mix food into it, as was explained above [in Halacha 3]
Squeezing into a liquid or a creamy dip: It is permitted to squeeze [fruits and pickled foods] into Muryas because it is considered a food however into liquids it is forbidden to squeeze them.
D. Squeezing out the food part of a fruit or cooked food:
Apples or other cooked fruits are allowed to be squeezed in order to remove from it all of its content because he is squeezing out all the food from it and is not [doing so] in order to take out its liquid.
Summary: Squeezing juice out of pickles and other foods saturated with external liquids:
Squeezing them in order to drink the liquid: Is Rabbinically forbidden
In order to enhance the food being squeezed: Permitted [directly into waist].
In order to place into food: It is permitted to squeeze it directly into food. However, to squeeze it into an empty vessel is forbidden even if one plans to place it into food.
Squeezing out the entire content of the food: Such as to squeeze out cooked apples from their peel is allowed.
 Admur 320:11; Michaber 320:7; Shmuel in Shabbos 145a
 Admur ibid; M”A 320:9, 12; M”B 320:29; Riy in Tosafus Kesubos 6a
 Admur ibid; Shmuel in Gemara ibid
 Admur 320:14; Michaber 320:8; Abayey Shabbos 145a
 Implication of M”A 320:12; P”M 320 A”A 12; M”B 320:31
 Shabbos Kehalacha Vol. 2 p. 440
 Admur 320:11; Michaber 320:7; Shabbos 145a
 Admur ibid; Rashi ibid; M”A 320:9
 Seemingly these items are not considered commonly squeezed and hence it is allowed to squeeze them to sweeten according to all, just as we rule by fruits that are not commonly squeezed.
 Shabbos Kehalacha Vol. 2 p. 424
 Michaber 320:7; M”B 320:24
 Tehila Ledavid 320:8; SSH”K 5:5; As rules Admur in 320:1
 Tzemach Tzedek in Piskei Dinim 320; Nishmas Adam 14 brought in Tehila Ledavid; Ketzos Hashulchan 126 footnote 26
 Shabbos Kehalacha Vol. 2 p. 424 [see there Biurim 13 and Tosefes Biur 20] based on Tzemach Tzedek in Piskei Dinim 320; Nishmas Adam 14 brought in Tehila Ledavid; Ketzos Hashulchan 126 footnote 26
 As he clearly rights in his reason “Since one does not need the liquid at all”. The words “at all” is in addition to the wording of the M”A ibid
 As Admur completely omits this allowance of the Michaber.
 So learns Shabbos Kehalacha 15:23 and so is implied from Ketzos Hashulchan ibid
 Ketzos Hashulchan 126 Footnote 19
 Shabbos Kehalacha Vol. 2 p. 446
 So rules Tehila Ledavid 320:14
 Shabbos Kehalacha Vol. 2 p. 425
 M”B 320:25 in name of Derisha regarding Lokshun
 However, the Chayeh Adam rules that oil is considered food, and it is hence permitted to squeeze it out even for a use, as one may separate a food from a food. [brought in M”B 320:25]
 Shabbos Kehalacha Vol. 2 p. 426
 Shabbos Kehalacha Vol. 2 p. 420
 Admur 320:12; Michaber 320:7; Tosafus Shabbos 145a
Other opinions: Some Poskim rule it is forbidden to squeeze cooked and pickled foods for the sake of their liquids even if one squeezes into other foods, and doing so contains a Biblical prohibition. [Michaber 320:7 in name of Rabbeinu Chananeil in Shabbos 125a in explanation of Rebbe Yochanan ibid; Rabbeinu Chananel concludes “We do not rule like Shmuel neither by Shabbos or Yom Tov and rather we rule like Rebbe Yochanan, and so we have received from our teachers”] Practically we do not rule like this opinion. [Admur ibid omits it completely from his Shulchan Aruch; Michaber 320:4 omitted it (however see Biur Halacha ibid); M”B 320:17 and 30] Nevertheless some Poskim conclude that one who is stringent is blessed. [M”B ibid; Teshuvas Harosh brought in Beis Yosef; Mishkanos Yaakov 112] According to Admur there is no need to be stringent at all. [See Shabbos Kehalacha 15 footnote 55]
 However the M”B  rules that one who is stringent to avoid squeezing these types of liquids even into food is to be praised.
 Admur ibid; Michaber ibid
 Admur 320:13; M”A 320:10; M”B 320:28
 A creamy dip made from fish fat.
 Admur 320:13; 320:10; M”A 320:10; M”B 320:28; Biur Halacha 320:4 “Haba Lechol” in name of Elya Raba 320:4
Other opinions: Some Poskim rule that even according to the stringent opinion it is permitted to squeeze “lemons and other fruits” into liquids. [Taz 320:5] As this is similar to squeezing the fruit for the sake of sweetening it. [P”M 320 M”Z 5] However this only refers to fruits that are not commonly squeezed, and hence require Achashvei to make them forbidden. However, those fruits that are commonly squeezed for their juice, and are hence forbidden according to all to be squeezed for their liquids, then it is likewise forbidden even according to the Taz to squeeze them into juice. [P”M ibid]
 Admur 320:15; Taz 320:5
 Admur 320:11
 Admur 320:11
 Admur 320:12
 Admur 320:15