CHIRP

FWIW, I was unable to reproduce this on Ubuntu or OS X.

On Windows, I think Python uses an internal CA bundle rather than the system's. RepeaterBook uses GoDaddy G2 CA. Apparently this isn't in the bundle.

I am having this same problem on a brand new Windows 10 laptop with the latest daily build 20180810. I tried disabling the Python SSL Certificate check by setting the environment variable PYTHONHTTPSVERIFY to 0 but that didn't work. All the other Python work around seem to involve code or importing certs or adding pip directories to your path. I did a bunch of research but couldn't get any of those workarounds to work.

Maybe you could just disable the SSL Certificate check for repeaterbook? The URL does not even appear to be HTTPS.

I think this code snippet will disable the check:

import ssl

try:
_create_unverified_https_context = ssl._create_unverified_context
except AttributeError:
# Legacy Python that doesn't verify HTTPS certificates by default
pass
else:
# Handle target environment that doesn't support HTTPS verification
ssl._create_default_https_context = _create_unverified_https_context

Here is error from the debug.log
C:\CHIRP\chirpw.exe\chirp\ui\inputdialog.py:106: GtkWarning: gtk_dialog_set_default_response: assertion `GTK_IS_DIALOG (dialog)' failed
http://www.repeaterbook.com/repeaters/downloads/chirp.php?func=default&state_id=41&band=%%&freq=%&band6=%&loc=%&county_id=051&status_id=%&features=%&coverage=%&use=%
Traceback (most recent call last):
File "chirp\ui\mainapp.pyo", line 1639, in mh
File "chirp\ui\mainapp.pyo", line 1015, in do_repeaterbook_political
File "urllib.pyo", line 98, in urlretrieve
File "urllib.pyo", line 245, in retrieve
File "urllib.pyo", line 213, in open
File "urllib.pyo", line 364, in open_http
File "urllib.pyo", line 377, in http_error
File "urllib.pyo", line 641, in http_error_302
File "urllib.pyo", line 667, in redirect_internal
File "urllib.pyo", line 213, in open
File "urllib.pyo", line 443, in open_https
File "httplib.pyo", line 1049, in endheaders
File "httplib.pyo", line 893, in send_output
File "httplib.pyo", line 855, in send
File "httplib.pyo", line 1274, in connect
File "ssl.pyo", line 352, in wrap_socket
File "ssl.pyo", line 579, in __init_
File "ssl.pyo", line 808, in do_handshake
IOError: [Errno socket error] [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:590)