I think my main mistake was forgetting that White doesn't reap the full benefit of her "gammons" after she takes the cube, because after some of Black's misses, she just has to cash.

              
 
              
 | | White is Player 2
score: 0 pip: 29 | Money session Jacoby | pip: 136 score: 0
Blue is Player 1 | |
| XGID=--BBBCB----------a--a-CcjA:2:1:1:00:0:0:1:0:10 |
| Blue on roll, cube action? |
| Analyzed in XG Roller+ |
| Player Winning Chances: | 63.43% (G: 18.62% B: 0.87%) |
| Opponent Winning Chances: | 36.57% (G: 24.56% B: 0.03%) |
| |
| Cubeless Equities |
| No Redouble: | +0.218 |
| Redouble: | +0.441 |
| |
| Cubeful Equities |
| No Redouble: | +0.301 (-0.103) |
| Redouble/Take: | +0.403 |
| Redouble/Drop: | +1.000 (+0.597) |
| |
| Best Cube action: Redouble / Take |
| |
eXtreme Gammon Version: 1.21
Variant:

              
 
              
 | | White is Player 2
score: 0 pip: 27 | Money session Jacoby | pip: 136 score: 0
Blue is Player 1 | |
| XGID=--BBBCB-----------a--aCcjA:2:1:1:00:0:0:1:0:10 |
| Blue on roll, cube action? |
| Analyzed in XG Roller+ |
| Player Winning Chances: | 55.22% (G: 16.59% B: 0.93%) |
| Opponent Winning Chances: | 44.78% (G: 31.10% B: 0.04%) |
| |
| Cubeless Equities |
| No Redouble: | -0.032 |
| Redouble: | -0.052 |
| |
| Cubeful Equities |
| No Redouble: | +0.044 |
| Redouble/Take: | -0.086 (-0.130) |
| Redouble/Drop: | +1.000 (+0.956) |
| |
| Best Cube action: No Redouble / Take |
| |
eXtreme Gammon Version: 1.21

              
 
              
 | | White is Player 2
score: 0 pip: 129 | Money session Jacoby Beaver | pip: 140 score: 0
Blue is Player 1 | |
| XGID=-bBBBBB----a-b----CbbccB--:3:-1:1:32:0:0:3:0:10 |
| Blue to play 32 |
| 1. | XG Roller+ | 18/16 18/15 | eq: -0.499 |
| Player: Opponent: | 44.47% (G:14.92% B:1.57%) 55.53% (G:29.50% B:2.82%) | |
|
| 2. | XG Roller+ | 6/4 6/3 | eq: -0.530 (-0.031) |
| Player: Opponent: | 39.64% (G:12.98% B:0.64%) 60.36% (G:22.65% B:1.22%) | |
|
eXtreme Gammon Version: 1.21
Variant:

              
 
              
 | | White is Player 2
score: 0 pip: 126 | Money session Jacoby Beaver | pip: 142 score: 0
Blue is Player 1 | |
| XGID=-bBBBBB----a-b----CbbbbbB-:1:1:1:32:0:0:3:0:10 |
| Blue to play 32 |
| 1. | XG Roller+ | 6/4 6/3 | eq: -0.544 |
| Player: Opponent: | 29.51% (G:9.12% B:0.48%) 70.49% (G:30.02% B:2.57%) | |
|
| 2. | XG Roller+ | 5/3 5/2 | eq: -0.603 (-0.059) |
| Player: Opponent: | 27.83% (G:8.00% B:0.37%) 72.17% (G:30.91% B:2.63%) | |
|
| 3. | XG Roller+ | 18/16 18/15 | eq: -0.809 (-0.265) |
| Player: Opponent: | 28.22% (G:6.19% B:0.55%) 71.78% (G:45.85% B:7.78%) | |
|
eXtreme Gammon Version: 1.21

              
 
              
 | | White is Player 1
score: 0 pip: 173 | | 11 point match | pip: 140 score: 0
Blue is Player 2 | |
| XGID=-aa-aBE-C--AdB-A-c-da---A-:0:0:1:00:0:0:0:11:10 |
| Blue on roll, cube action? |
| Analyzed in XG Roller+ |
| Player Winning Chances: | 65.76% (G: 30.34% B: 2.60%) |
| Opponent Winning Chances: | 34.24% (G: 6.88% B: 0.35%) |
| |
| Cubeless Equities |
| No Double: | +0.578 |
| Double: | +1.187 |
| |
| Cubeful Equities |
| No Double: | +0.796 (-0.128) |
| Double/Take: | +0.924 |
| Double/Drop: | +1.000 (+0.076) |
| |
| Best Cube action: Double / Take |
| |
eXtreme Gammon Version: 1.21, MET: Rockwell-Kazaross