Hello! Today I can start all my apps with Microsoft-IIS/10.0, Python 3.7.3 
and fdb driver. I use that web.config:
<?xml version="1.0" encoding="UTF-8"?>
<!-- app configuration for web2py on IIS -->
<configuration>
  <appSettings>
    <add key="WSGI_HANDLER" value="gluon.main.wsgibase" />
    <add key="WSGI_RESTART_FILE_REGEX" value=".*((routes\.py)|(\.config))$" 
/>
  </appSettings>
  <system.webServer>
    <rewrite>
      <rules>
        <clear />
        <rule name="static" enabled="true" stopProcessing="true">
          <match url="^(\w+)/static(?:/_[\d]+\.[\d]+\.[\d]+)?/(.*)$" />
          <conditions logicalGrouping="MatchAll" trackAllCaptures="false" />
          <action type="Rewrite" url="applications/{R:1}/static/{R:2}" 
logRewrittenUrl="false" />
        </rule>
        <rule name="web2py_app" enabled="true" stopProcessing="true">
          <match url="(.*)" ignoreCase="false" />
          <conditions logicalGrouping="MatchAll" trackAllCaptures="false" />
          <action type="Rewrite" url="handler.web2py/{R:1}" 
appendQueryString="true" />
        </rule>
      </rules>
      <outboundRules>
        <rule name="static_version_cache_control" 
preCondition="static_version">
          <match serverVariable="RESPONSE_Cache-Control" pattern=".*" />
          <action type="Rewrite" value="max-age=315360000" />
          <conditions>
          </conditions>
        </rule>
        <rule name="static_version_Expires" preCondition="static_version">
          <match serverVariable="RESPONSE_Expires" pattern=".*" />
          <action type="Rewrite" value="Thu, 31 Dec 2037 23:59:59 GMT" />
        </rule>
        <preConditions>
          <preCondition name="static_version">
            <add input="{REQUEST_URI}" 
pattern="(\w+)/static(?:/_[\d]+\.[\d]+\.[\d]+)?/(.*)$" />
          </preCondition>
        </preConditions>
      </outboundRules>
    </rewrite>
  </system.webServer>
</configuration>


-- 
Resources:
- http://web2py.com
- http://web2py.com/book (Documentation)
- http://github.com/web2py/web2py (Source code)
- https://code.google.com/p/web2py/issues/list (Report Issues)
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