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  (1) Posted by Frank Richter [Saturday, Mar 1, 2014 10:26]  Helpmate question What is the longest helpmate with castling (black or white, both are interesting)?   (2) Posted by Kevin Begley [Saturday, Mar 1, 2014 12:07]; edited by Kevin Begley [140301]  Maybe there are longer, but here's what I find...
With Fairy Elements:
Arnold Beine, Die Schwalbe, 2004
h#50 (4+3) C+
No Fairy Elements:
Miloš Tomašević & Radovan Tomašević, Mat 1986
(= 2+9 ) h#9 (2+9) C+
1.Se7 Kb1 2.00 Kc1 3.Rc8+ Kd2 4.Rc3 bxc3 5.g4 c4 6.g3 cxd5 7.g2 d6 8.g1=R dxe7 9.Rg7 e8=Q#
Incidentally, seems there was a TT for this, in 1986, where Miloš & Radovan took 1st Prize with a somewhat similar h#8.5 realization, which did not require the black Knight (obviously a flaw, but the above is published strictly for record purposes  not as a version).
Note: 1968, Roman Zalokotsky published a similar h#7  orthodox, with twin b) bRa8>h8  where black castles both ways.
If you want both sides to castle, it's a more difficult search... but, for orthodox, I have not found anything in 6.5 moves, or more...   (3) Posted by Frank Richter [Saturday, Mar 1, 2014 15:51]  Many thanks, Kevin.
I found also P0503638, Milos Tomasevic, Radovan Tomasevic, 167v KleinWinsener RochadeTT 19811984, 3rd Prize, h#9 (2+9). So there seems to be still no orthodox h# with castling in 10 or more moves.   (4) Posted by Kevin Begley [Saturday, Mar 1, 2014 19:40]; edited by Kevin Begley [140301]  You're welcome, Frank.
Seems I made an error.
Win Chloe shows the h#8.5 (P0503638) as 3rd Prize (not 1st), a version from: 1st TT, Klein Winsener Rochade, 1986.
The dates differ slightly, between databases.
And, it appears in the FIDE Album: "E224 p.382, Album FIDE 198688" (likely as the previous version).   (5) Posted by Kostas Prentos [Saturday, Mar 1, 2014 20:32]; edited by Kostas Prentos [140301]  I did a quick search in WinChloe for orthodox helpmates in which both sides castle. Surprisingly, there are only two problems in 5 moves. I suppose, nobody cared to try for a longer helpmate, because it seems rather easy to go up to at least 6 moves.
R.Zalokotsky & V.Shum, V. Kirillov55 JT, 2006, 3rd comm.
(= 3+9 ) h#5 2 solutions
1.Kd7 Kd1 2.Kc6 Kc2 3.Kb5 Kxb2 4.Ka4 Kc3 5.Ka3 Ra1#
1.Sb7 00 2.000 Rc1 3.Kb8 Rxc5 4.Ka8 Rc6 5.Rb8 Ra6#
K.Prentos, Orbit 2009, 4th comm.
(= 7+15 ) h#5
1.Ba6 Ba5 2.Rb5 00 3.Rb6 Re1 4.000 Rxe7 5.Rb8 Rc7#
EDIT: I just realized that in the first problem, White's last move must have been with the King or Rook. This means that the second solution is not possible, because White's castling is not allowed. Maybe an oversight by the composers and the judge?   (6) Posted by Rewan Demontay (Real Name: James Malcom) [Thursday, Oct 3, 2019 20:49]; edited by Rewan Demontay (Real Name: James Malcom) [191003]  Here’s another h#5 where both sides castle, but this time there is castling on the same side instead!
YACPDB #342442 or on SuperProblem (Orgingal Source): http://popovgl.narod.ru/Bliz/Bliz32itog.html
Кройтор, Михаил Васильевич
TT32, SuperProblem 20120506
7th Place
BTM, h#5
(= 7+10 )
  (7) Posted by Vitaly Medintsev [Thursday, Oct 3, 2019 23:38]  In PDB the longest is P0533781  h#9 with black 00. See also P0503638  h#8.5 with black 000.
Here is the search query: g='h#' and (sol='00' or sol='000') AND (STIP='h#7' or STIP='h#8' or STIP='h#9' or STIP='h#10' or STIP='h#11')   (8) Posted by Rewan Demontay (Real Name: James Malcom) [Tuesday, Nov 5, 2019 23:08]  I recently found a h#6 where both sides castle. A new record!
WTM, h#6, C+
P1356169
Zlatko Mihajloski
H4125 The Problemist 268, p. 319, 03/2018
(= 2+11 )
  (9) Posted by Viktoras Paliulionis [Wednesday, Nov 6, 2019 00:04]  Four castling:
P0525380
Julius DohrnLüttgens
769 FEENSCHACH 08/1951
(= 12+9 )
h#4 2.1...
1. 000 000 2. Rxd3 Rxd3 3. Rh7 Rhd1 4. Rc7 Rd8#
1. 00 00 2. Rxf2 Rxf2 3. Ra7 Raf1 4. Rg7 Rf8#   (10) Posted by Rewan Demontay (Real Name: James Malcom) [Wednesday, Nov 6, 2019 02:58]  Another problem with 4 castlings.
h#4
P0003737
Tivadar Kardos
4528 ArbejderSkak 08/1957
(= 9+16 )
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MatPlus.Net Forum General Helpmate question 


