diff --git a/trains/backend_api/session/session.py b/trains/backend_api/session/session.py
index ade77ae0..6baa4e4a 100644
--- a/trains/backend_api/session/session.py
+++ b/trains/backend_api/session/session.py
@@ -441,7 +441,7 @@ class Session(TokenManager):
 
         # return default
         host = cls.get_api_server_host(config)
-        if host == cls.default_host:
+        if host == cls.default_host and cls.default_web:
             return cls.default_web
 
         # compose ourselves
@@ -468,7 +468,7 @@ class Session(TokenManager):
 
         # return default
         host = cls.get_api_server_host(config)
-        if host == cls.default_host:
+        if host == cls.default_host and cls.default_files:
             return cls.default_files
 
         # compose ourselves
diff --git a/trains/config/default/__main__.py b/trains/config/default/__main__.py
index 13d106a1..997e9c1e 100644
--- a/trains/config/default/__main__.py
+++ b/trains/config/default/__main__.py
@@ -1,10 +1,10 @@
 from __future__ import print_function
 
 from six.moves import input
-from ...utilities.pyhocon import ConfigFactory
 from pathlib2 import Path
 from six.moves.urllib.parse import urlparse
 
+from trains.utilities.pyhocon import ConfigFactory
 from trains.backend_api.session.defs import ENV_HOST
 from trains.backend_config.defs import LOCAL_CONFIG_FILES
 from trains.config import config_obj
@@ -78,20 +78,24 @@ def main():
         web_host = ''
         files_host = ''
         if not parsed_host.port:
-            print('Host port not detected, do you wish to use the default 8008 port n/[y]? ', end='')
+            print('Host port not detected, do you wish to use the default 8080 port n/[y]? ', end='')
             replace_port = input().lower()
             if not replace_port or replace_port == 'y' or replace_port == 'yes':
                 api_host = parsed_host.scheme + "://" + parsed_host.netloc + ':8008' + parsed_host.path
                 web_host = parsed_host.scheme + "://" + parsed_host.netloc + ':8080' + parsed_host.path
                 files_host = parsed_host.scheme + "://" + parsed_host.netloc + ':8081' + parsed_host.path
+            elif not replace_port or replace_port.lower() == 'n' or replace_port.lower() == 'no':
+                web_host = input_host_port("Web", parsed_host)
+                api_host = input_host_port("API", parsed_host)
+                files_host = input_host_port("Files", parsed_host)
         if not api_host:
             api_host = parsed_host.scheme + "://" + parsed_host.netloc + parsed_host.path
 
     api_host = input_url('API Host', api_host)
     files_host = input_url('File Store Host', files_host)
 
-    print('\nTRAINS Hosts configuration:\nAPI: {}\nWeb App: {}\nFile Store: {}\n'.format(
-        api_host, web_host, files_host))
+    print('\nTRAINS Hosts configuration:\nWeb App: {}\nAPI: {}\nFile Store: {}\n'.format(
+        web_host, api_host, files_host))
 
     while True:
         print(description.format(web_host), end='')
@@ -167,16 +171,28 @@ def input_url(host_type, host=None):
         parse_input = input()
         if host and (not parse_input or parse_input.lower() == 'yes' or parse_input.lower() == 'y'):
             break
-        if parse_input and verify_url(parse_input):
-            host = parse_input
+        parsed_host = verify_url(parse_input) if parse_input else None
+        if parse_input and parsed_host:
+            host = parsed_host.scheme + "://" + parsed_host.netloc + parsed_host.path
             break
     return host
 
 
+def input_host_port(host_type, parsed_host):
+    print('Enter port for {} host '.format(host_type), end='')
+    replace_port = input().lower()
+    return parsed_host.scheme + "://" + parsed_host.netloc + (':{}'.format(replace_port) if replace_port else '') + \
+           parsed_host.path
+
+
 def verify_url(parse_input):
     try:
         if not parse_input.startswith('http://') and not parse_input.startswith('https://'):
-            parse_input = 'http://' + parse_input
+            # if we have a specific port, use http prefix, otherwise assume https
+            if ':' in parse_input:
+                parse_input = 'http://' + parse_input
+            else:
+                parse_input = 'https://' + parse_input
         parsed_host = urlparse(parse_input)
         if parsed_host.scheme not in ('http', 'https'):
             parsed_host = None