When executing the installer with arguments or using the unattend.xml to run it without UI as documented in https://python.readthedocs.io/en/stable/using/windows.html#installing-without-ui the installer ignores the arguments or unattend.xml when it's executed again.

The second time, the installer (running i modify mode) uses the default values (hereby removing the Prepenpath if set the first time)

(testet with version 3.6.6-amd64 to 3.7.3-amd64 of the executable installer)

To recreate, run the following : 

step 1 :
python-3.6.6-amd64.exe /passive InstallAllUsers=1 PrependPath=1 Include_doc=0 Include_dev=0 Include_tcltk=0 Include_test=0 SimpleInstall=1 

now python is install as expected.

step 2 : 
python-3.6.6-amd64.exe /passive InstallAllUsers=1 PrependPath=1 Include_doc=0 Include_dev=0 Include_tcltk=0 Include_test=0 SimpleInstall=1

even though the options are exactly the same, the installer now removes python from path and installs tcltk, documentation, test and dev.

step 3 : 
python-3.6.6-amd64.exe /passive InstallAllUsers=1 PrependPath=1 Include_doc=0 Include_dev=0 Include_tcltk=0 Include_test=0 SimpleInstall=1

now the installer only makes a quick check, what i would have expected in step 2, but hare only the default values are used.

Hmm... interesting.

Thanks for the heads-up, I think I know what this may be (there's a conditional planning stage in the bootstrapper that is probably being skipped on Modify). I'll take a look when I get a chance.

Okay, this is definitely an ordering issue in Tools/msi/bundle/bootstrap/PythonBootstrapApplication.cpp

Fixing most of the options is easy - just a case of moving LoadOptionalFeatureStates() a few lines up - but Install_launcher is set much later. I should be able to fix both though.

New changeset 3a0ddbcdfcbc0f4372905fabf81e093f1b043e99 by Steve Dower in branch 'master':
bpo-37283: Ensure command-line and unattend.xml setting override previously detected states in Windows installer (GH-15759)
https://github.com/python/cpython/commit/3a0ddbcdfcbc0f4372905fabf81e093f1b043e99

New changeset 2a4a982cbccf66dd8d29439dbd232c79fe3ec44e by Miss Islington (bot) in branch '3.8':
bpo-37283: Ensure command-line and unattend.xml setting override previously detected states in Windows installer (GH-15759)
https://github.com/python/cpython/commit/2a4a982cbccf66dd8d29439dbd232c79fe3ec44e

New changeset d3b8a6bf7c5f7574a3256468c4d0a755ba7a9048 by Miss Islington (bot) in branch '3.7':
bpo-37283: Ensure command-line and unattend.xml setting override previously detected states in Windows installer (GH-15759)
https://github.com/python/cpython/commit/d3b8a6bf7c5f7574a3256468c4d0a755ba7a9048

This will be fixed in the next release. Thanks for the report!