We have more or less the same configuration with no issues.

One thing that might help you though 
You can setup the admin app to work over https:

https://www.youtube.com/watch?v=_4to_44DcJU  time :   46:15

Run from web2py base folder :

For 2.7 :

from gluon.main import save_password; save_password(raw_input('admin 
password: '),443)

For 3.x

from gluon.main import save_password; save_password(input('admin password: 
'),443)

but otherwise you should be able to run the admin via http from the server.

Good luck,
David


On Tuesday, October 22, 2019 at 8:25:34 AM UTC+2, martel berends wrote:
>
> I'm trying to deploy a web2py server with the following specs:
> - Windows server 2019
> - IIS 10
> - Python 3.5 above
>
> I followed the deployment scripts in de manual (
> http://web2py.com/books/default/chapter/29/13/deployment-recipes#IIS) and 
> the excellent video of Remco Boerma (https://youtu.be/gxOhsThD0FY) 
>
> I've the basic site working, but when I go to the admin section, an error 
> occurs :
>
> Error occurred:
>
> Traceback (most recent call last):
>   File "c:\python36-32\lib\site-packages\wfastcgi.py", line 851, in main
>     response.send(FCGI_STDOUT, part)
>   File "c:\python36-32\lib\site-packages\wfastcgi.py", line 756, in send
>     return send_response(self.stream, self.record.req_id, resp_type, content, 
> streaming)
>   File "c:\python36-32\lib\site-packages\wfastcgi.py", line 370, in 
> send_response
>     raise TypeError("content must be encoded before sending: %r" % content)
> TypeError: content must be encoded before sending: 'a'
>
>
> I've tried python 3.4 / 3.5 / 3.6 and 3.7 but all with the same result. Going 
> back to 2.7 is not what I want, due to end-of-life of python 2.7 and my site 
> is coded in Python 3. 
>
> I've installed the source-code version of web2py and the user-registration in 
> the standard welcome application is working fine. So the patform seems to 
> work. 
>
>
> It's something between web2py and wfastcgi, but I've no clue what is causing 
> this error and how to solve it. 
>
>
> Any help would be fantastic. 
>
>

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