The Boleslavsky is a positional approach and suits patient players well who find uncompromising kingside attacks too unnerving. Both sides will typically castle on the kingside. There will be some similarities to certain Najdorf positions (especially those systems with a White bishop on e2).White will try to use the d5-square, while Black typically seeks active counter play on the queenside.
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Our starting position typically arises after 1.e4 c5 2.Nf3 Nc6 3.d4 cxd4 4.Nxd4 Nf6 5.Nc3 d6 (or 2…d6 and 5…Nc6). We are now looking at a solid system for White where he will try to limit Black’s active options.

6.Bb5 looks stronger than it is. After 6…Bd7, the pin is broken and Black will have no problems getting equal chances.

6.Be2 is one of the many fine moves in this position and is a more patient and positional approach than for example 6.Bc4, which often leads to the Velimirovic attack or to the Sozin. White can also play 6.Bg5, which leads to a Richter-Rauzer. All of these systems are examined in other challenges

6…e5 fights back in the center like Black does in many Najdorf positions (where Black plays 5…a6 instead of 5…Nc6). This gives White control over the d5-square, but Black hopes to balance this by getting active piece play. Note that 6…e6 instead will likely lead to a Scheveningen, while 6…g6 invites White to play a Classical Dragon.
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White has to make the first important strategic decision.

7.Nb3 is a reasonable move, but allows Black to continue with the same plan as he uses against the Be2 Najdorf (with bishops on e7 and e6). However, Black could save a tempo by not playing …a7-a6. While 7.Nb3 is playable for White, Black has done well against it in practice.

7.Nf5? allows Black to gain the center by exchanging pawns with 7…Nxe4! 8.Nxg7+ Bxg7 9.Nxe4 d5. Remember this motif, it is quite common in such positions.

7.Nf3 is considered best and shows Black that this will be a positional battle where White will likely refrain from kingside play such as f2-f4. White could also consider 7.Nxc6, when …bxc6 8.Qd3! Be7 9.Qg3 0-0 10.0-0 Be6 11.f4 (Hort-Shamkovich, 1962) is an interesting attempt to play on the kingside. Note that 7.Nb3 is playable, but that Black has done well against it by choosing the normal Najdorf setup against it (with bishops on e7 and e6). In that line Black should save a tempo and not play …a7-a6.

7…h6 is by far the most popular move nowadays. Black wants to avoid giving White the option of pinning the f6-knight with 8.Bg5 next, when White could exchange Black’s best defender of the critical d5-square for the g5-bishop. Later Black also wants to develop the light- squared bishop to e6 without having to worry about White playing Ng5.
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White’s bishops will not be as aggressively developed as in many other Open Sicilians.

8.0-0 castles kingside as no other urgent matters take precedence. Now White’s king will be safe, while the kingside rook can join forces with White’s other pieces.

8…Be7 develops the kingside bishop to its only square. Note that this bishop is limited by its own center pawns on d6 and e5. But it will often be an important defender in these types of positions. If Black plays 8…Be6 instead, play usually transposes soon.
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Both sides can calmly develop all of their pieces in this position as there is little confrontation yet.

9.Nd2? moves the f3-knight again and gets it in the way of other pieces. Black could also consider playing …Nd4 soon. Now try to improve the position of your dormant minor piece instead.

9.Be3 apparently moves this bishop to its best square. But on e3 it often gets in the way of a White rook on e1 later. Your move is playable, but we prefer considering a different option for this bishop.

9.Bd2? tries to develop the bishop, but on d2 it would only be in the way of your queen. Now find a better way to develop this bishop.

9.b3 looks a bit odd at first, since it leaves the knight on c3 unprotected. But Black is unable to take advantage of this temporary condition as you could take care of this on the following move. One other advantage of this move is that Black will not be able to use the c4- square for his pieces. This is often a popular plan for Black in these types of positions. Note that the main line of this variation begins with 9.Re1 instead. Then play is balanced after 9…0-0 10.h3 Be6 11.Bf1.

9…0-0 castles on the kingside as well. Both sides will find it difficult to generate any activity against the opponent’s king in this system. Note that play would likely transpose if Black played 9…a6 or 9…Be6 instead.
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White’s patient approach may appear to be boring to tactical players, but a good player needs to be versatile and at home in many different kinds of positions.

10.Bb2 fianchettoes the dark-squared bishop as there were no better alternatives on the c1-h6 diagonal. It may appear that this bishop has little to do on b2, but one of the functions of it is to pressure Black’s e5-pawn and make it difficult for Black to play the freeing …d6-d5 pawn advance later on.

10…a6 hopes to gain some space on the queenside next. This is a common idea in Sicilians. If 10…Be6, then 11.Re1 Rc8 12.Bf1 gives White a small edge.
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It’s important to pay close attention to the opponent’s plans.

There is no gain in moving the c3- knight right now. In fact, you just invited Black to win a pawn with 11…Nxe4.

11.a4 prevents Black from playing …b7-b5 next and gains space on the queenside. Playing a4 after Black has advanced …a7-a6 is a very common theme in Open Sicilians. White may now consider using the c4-square for his pieces later on. Former World Champion Vasily Smyslov has tried two other moves in this position, but Black was fine after both 11.Re1 b5 12.Bd3 Bb7 13.a4 b4 (Smyslov-Gligoric, 1977) and 11.Nd2 Nd4 12.Bd3 b5 13.Re1 Bb7 (Smyslov-Timman, 1977).

11…Be6 places the bishop on a good square from where it covers the important d5-square. Black will try to make it undesirable for White to play Nc3-d5 in these positions and will even try to get rid of the backward d-pawn by playing d6-d5 at the right time. In Yemelin-Lukin (1995), Black instead tried 11…Qc7 12.Re1 Bd7 13.Bf1 Rac8, but White could already consider 14.Nd5 in this position.
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If Black could play …d6-d5 in this kind of position without losing the e5-pawn, he usually reaches at least equality.

12.Rc1 moves the rook to a square which could turn out to be good if White is able to play Nc3-d5 and c2-c4 later. But this is not possible without some preparation. You would do better to prepare this maneuver first.

12.Re1 appears like a strange move at first, but it has several subtle qualities. From e1, the rook will soon protect the e4-pawn and thus give White’s c3-knight the option to go to d5. The rook also pressures Black’s e5-pawn indirect and thus makes it more difficult for Black to play the freeing pawn break …d6-d5. Both 12.Nd2 Rc8 13.Re1 Nd4 14.Bd3 Bg4 15.f3 and 12.Qd2 Rc8 13.Rfe1 Qa5 14.Rac1 Bd8 would be unclear, while 12.h3 will likely transpose.

12…Rc8 gets the rook on the half-open c-file where it hopes to pressure White’s knight on c3 or the pawn on c2 later on. Note that 12…d5? would lose the e5-pawn following 13.exd5 Nxd5 14.Nxd5 Qxd5 15.Qxd5 Bxd5 16.Nxe5.
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Playing the correct move order often makes all the difference when trying to reach a desired position.

13.Bd3?! protects the e4-pawn, but gets in the way of White’s queen and reduces White’s control of the important d5- square. Black could now play 13…Rfe8. Then only the moves …Qc7 and …Bf8 are required before Black could play the desired …d6-d5 pawn break. This bishop has a much better square to go to where it won’t be in the way of other pieces anymore.

13.h3 is the most accurate move in this position. Besides giving the White monarch an escape square off the back rank, this move also prevents Black’s pieces from using the g4-square. Common is also 13.Bf1, but then Black may try 13…Bg4 (other moves such as 13…Qd7 or 13…Nb4 are also interesting and would probably transpose).

13…Nb4 is a fine move now that White has played a2-a4. The knight is relatively secure on b4, controls the vital d5- square and also, in combination with the rook on c8, pressures White’s c2- pawn.
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Black has been able to score a little better with the Boleslavsky than with other approaches.

14.Qd2 connects the rooks, but is harmless after 14…Qc7 and 15…Rfd8. We prefer keeping the d2-square vacant for another piece.

14.Ba3 attacks Black’s b4-knight, but leaves the horse on c3 unprotected. Play would be double-edged after 14…Qb6 15.Qd2. We prefer keeping the bishop on b2 for the long term as it will have some influence over the center soon.

14.Nd2 is a good move now that Black’s queenside knight can no longer go to d4. In the game Brooks-De Firmian (1990) Black reached a fine position with 14…Qc7 15.Bc4 Rfd8 16.Rc1 Qa5. But we believe that White can improve on this game with 15.Nc4!?, e.g., 15…Nxe4?! 16.Nxe4 d5 17.Bxe5 or 15…Rad8!? 16.Ne3 d5 (else 17.Bf3 will give White an edge) 17.exd5 Nbxd5 18.Ncxd5 Nxd5 19.Nxd5 Bxd5 20.Bd3, and White will have a slight initiative due to the pressure against Black’s e5-pawn and Qg4 coming soon. If 19…Rxd5 instead, then 20.Bd3 and 21.Qe2 may give White a small edge.

14.Bf1 gets this bishop out of the way of the rook on e1 and allows this rook to protect the e4-pawn and stop Black from playing …d6-d5 soon by pressuring the e5-pawn indirectly. If White plays 14.Nd2 instead, then Black can reach a satisfactory position with 14…Qc7 15.Bc4 Rfd8 16.Rc1 Qa5 (Brooks-De Firmian, 1990). But we believe that White can improve on this game with 15.Nc4!?, e.g., 15…Nxe4?! 16.Nxe4 d5 17.Bxe5 or 15…Rfd8!? 16.Ne3 d5 (else 17.Bf3 will give White an edge) 17.exd5 Nbxd5 18.Ncxd5 Nxd5 19.Nxd5 Bxd5 20.Bd3, and White will have a slight initiative due to the pressure against Black’s e5-pawn and Qg4 coming soon. If 19…Rxd5, then 20.Bd3 and 21.Qe2 may give White a small edge. 
Following 14.Bf1, Black continued with 14…Re8 in the game Osnos- Maharichev (1978). Then 15.Nd2 Bf8 16.Nc4 Nxe4 17.Nxe4 d5 18.Ned6 gives White some pressure on the dark squares after 18…Bxd6 19.Nxd6 Qxd6 20.Bxe5. This variation was better for White due to his bishop pair even though Black was able to remove White’s e4-center pawn and control over the d5-square. Note that White would have played 17.Ne3 with control over d5 had Black not played 16…Nxe4. We believe that Black should play 14…Qc7 instead. Then 15.Rc1 Rfd8 16.Nd2 would lead to a position that is typical for this system. If Black is able to play …d6-d5 in the next few moves, he will be roughly equal.

If White is allowed to gain control of the key d5-square by playing Nd2-c4-e3, however, Black will have no easy road to equality. One of the many possible lines is 16…Bf8 17.Qf3 d5 18.Nxd5 Nfxd5 19.exd5 Bxd5 20.Qg3 f6 21.Ne4 with an unclear position. 
In many of the above lines we saw that Black had to play …d6-d5 at some time in order to avoid getting smothered. But after pawns were exchanged in the center, White often maintains a slight edge due to his kingside play and pressure against the e5-pawn with the strong bishop on b2. This bishop often comes to life later in the game. The setup with the bishop on b2 and pawns on b3 and a4 also allows White to use the c4-square in some lines. This square is usually firmly in Black hands in these kind if middle game positions. 
Both players need to be patient in the Boleslavsky as the slightest positional slip could give the opponent a permanent pull on the position. If you like these types of positions for White, take a look at the main line starting with 9.Re1 as well. Should you be in the mood for more tactics right out of the opening, you can choose from many sharper systems at move six.