I ran with a log and this was what I got.
Running launcher: Fallout (StartMenu.C^3A_users_crossover_Start+Menu/Programs/Steam/Fallout.url)
Command-line options:
Bottle: Fallout
Debug channels:
CrossOver 16.2.5.30228
OS X 10.12.6
Install location: /Applications/CrossOver.app
Mac Locale: en_US
CXConfig->read(/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/etc/CrossOver.conf)
CXConfig->read(/Users/vab798dg3/Library/Application Support/CrossOver/CrossOver.conf)
13303: Grabbing the '/var/folders/ql/wk8r37l53p19q1msd_jntlbc0000gn/T//.wine-501/bottle-1000004-56bf32.lock' lock
13303: Got the '/var/folders/ql/wk8r37l53p19q1msd_jntlbc0000gn/T//.wine-501/bottle-1000004-56bf32.lock' lock
CXConfig->read(/Users/vab798dg3/Library/Application Support/CrossOver/Bottles/Fallout/cxbottle.conf)
13303: Releasing the '/var/folders/ql/wk8r37l53p19q1msd_jntlbc0000gn/T//.wine-501/bottle-1000004-56bf32.lock' lock
Bottle environment variables:
CX_BOTTLE_CREATOR_APPID -> com.codeweavers.c4.3451
CXRWConfig->new(/Users/vab798dg3/Library/Application Support/CrossOver/Bottles/Fallout/cxmenu.conf)
'/Users/vab798dg3/Library/Application Support/CrossOver/Bottles/Fallout/cxmenu.conf' not modified -> no need to save
Starting 'StartMenu.C^3A_users_crossover_Start+Menu/Programs/Steam/Fallout.url'
system encoding='UTF-8'
Exec-ing '"/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/bin/wine" --bottle "Fallout" --check --wait-children --start "C:/users/crossover/Start Menu/Programs/Steam/Fallout.url" --cx-log -'
fixme:exec:SHELL_execute flags ignored: 0x00000100
fixme:ntdll:NtLockFile I/O completion on lock not implemented yet
fixme:ver:GetCurrentPackageId (0x33e500 0x0): stub
fixme:process:ProcessIdToSessionId Unsupported for other processes.