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An interesting event happened during my session yesterday regarding Shield Slam. So, I have some questions.
Player A was attacking Enemy with Shield Slam, with Players B, C, and D lined up behind them in a row. Player D had his back to a wall.
It looked something like this....
| Plyr A | Enemy | Plyr B | Plyr C | Plyr D |||
Player A successfully Shield Slams Enemy with Bull Rush.
1. Does Player A need to roll a d20 for the Bull Rush as a separate combat manuever, or does he use the same roll he made with his Shield Bash?
2. The Bull Rush attempt against Player B use the same Bull Rush roll as he made against Enemy?
3. Does Player A need to make Bull Rush attempts against Players C and D?
4. Is the -4 penalty to Bull Rush for the character behind the creature being bull rushed supposed to be cumulative for each character? Is this penalty applied to all Bull Rush attempts after the 1st or cumulative (-4 vs Player B, -8 vs Player C, -12 vs Player D).
5. Who falls prone is this scenario? Everyone in the same square at the wall? The square they are currently occupy if the Bull Rush is successful?
Thank you.

Coolwasabi |

As far as I can tell, the initial enemy would use the shield bash attack roll, each player afterwards uses a separate bullrush attempt at the stacking -4penalty. If all are a success, Player D would be knocked prone and all the other targets would shift towards the wall 1 space and DM would probably have to decide if any players shift to a square to not occupy the same space.
If Plyr A decided to move with the bullrush, depending on their successes they can potentially push plyr C 10 ft to be knocked prone, or plyr B 15 ft and the Enemy 20ft to knock all prone, and the DM would asign which squares people end up in afterwards.
Otherwise Plyr A can just opt to not bullrush at all.

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1. Does Player A need to roll a d20 for the Bull Rush as a separate combat manuever, or does he use the same roll he made with his Shield Bash?
Same roll; "Any opponents hit by your shield bash are also hit with a free bull rush attack, substituting your attack roll for the combat maneuver check"
2. The Bull Rush attempt against Player B use the same Bull Rush roll as he made against Enemy?
No, new roll at -4; "If there is another creature in the way of your bull rush, you must immediately make a combat maneuver check to bull rush that creature. You take a –4 penalty on this check for each creature being pushed beyond the first."
3. Does Player A need to make Bull Rush attempts against Players C and D?
It depends. If the initial bull rush on the Enemy only exceeded their CMD by 4 or the bull rush against Player B failed then you can't attempt to push C. If the Enemy CMD was beat by 9 or less, Player B beat by 4 or less, OR the rush against Player C failed then you can't attempt to push D.
"If you are successful, you can continue to push the creatures a distance equal to the lesser result. For example, if a fighter bull rushes a goblin for a total of 15 feet, but there is another goblin 5 feet behind the first, he must make another combat maneuver check against the second goblin after having pushed the first 5 feet. If his check reveals that he can push the second goblin a total of 20 feet, he can continue to push both goblins another 10 feet (since the first goblin will have moved a total of 15 feet)."
4. Is the -4 penalty to Bull Rush for the character behind the creature being bull rushed supposed to be cumulative for each character? Is this penalty applied to all Bull Rush attempts after the 1st or cumulative (-4 vs Player B, -8 vs Player C, -12 vs Player D).
Yes, -4 for B, -8 for C, -12 for D. See quotation under 2 above.
5. Who falls prone is this scenario? Everyone in the same square at the wall? The square they are currently occupy if the Bull Rush is successful?
Again, it depends on how far you are pushing each creature. If you push the Enemy 30 feet, but fail to push B then nobody will be knocked prone. Conversely, if you push the Enemy 20+ feet, B 15+ feet, C 10+ feet, AND D 5+ feet then ALL of them fall prone.