diff --git a/addons/fetchmail/models/fetchmail.py b/addons/fetchmail/models/fetchmail.py
index da83677a02c..0850f5e19ee 100644
--- a/addons/fetchmail/models/fetchmail.py
+++ b/addons/fetchmail/models/fetchmail.py
@@ -3,6 +3,8 @@
 
 import logging
 import poplib
+from ssl import SSLError
+from socket import gaierror, timeout
 from imaplib import IMAP4, IMAP4_SSL
 from poplib import POP3, POP3_SSL
 
@@ -124,7 +126,15 @@ odoo_mailgate: "|/path/to/odoo-mailgate.py --host=localhost -u %(uid)d -p PASSWO
             try:
                 connection = server.connect()
                 server.write({'state': 'done'})
-            except Exception as err:
+            except UnicodeError as e:
+                raise UserError(_("Invalid server name !\n %s", tools.ustr(e)))
+            except (gaierror, timeout, IMAP4.abort) as e:
+                raise UserError(_("No response received. Check server information.\n %s", tools.ustr(e)))
+            except (IMAP4.error, poplib.error_proto) as err:
+                raise UserError(_("Server replied with following exception:\n %s", tools.ustr(err)))
+            except SSLError as e:
+                raise UserError(_("An SSL exception occurred. Check SSL/TLS configuration on server port.\n %s", tools.ustr(e)))
+            except (OSError, Exception) as err:
                 _logger.info("Failed to connect to %s server %s.", server.server_type, server.name, exc_info=True)
                 raise UserError(_("Connection test failed: %s", tools.ustr(err)))
             finally:
diff --git a/addons/mail/views/res_config_settings_views.xml b/addons/mail/views/res_config_settings_views.xml
index 617e3449ce5..4e7e69ccd3d 100644
--- a/addons/mail/views/res_config_settings_views.xml
+++ b/addons/mail/views/res_config_settings_views.xml
@@ -31,6 +31,7 @@
                             </div>
                             <div class="o_setting_right_pane">
                                 <label for="external_email_server_default"/>
+                                <a href="https://www.odoo.com/documentation/user/13.0/discuss/advanced/email_servers.html" title="Documentation" class="o_doc_link" target="_blank"></a>
                                 <div class="text-muted" id="external_email_server_default">
                                     Configure your own email servers
                                 </div>
diff --git a/odoo/addons/base/models/ir_mail_server.py b/odoo/addons/base/models/ir_mail_server.py
index ad8f03ca637..f589b103a7c 100644
--- a/odoo/addons/base/models/ir_mail_server.py
+++ b/odoo/addons/base/models/ir_mail_server.py
@@ -9,6 +9,8 @@ import email.policy
 import logging
 import re
 import smtplib
+from socket import gaierror, timeout
+from ssl import SSLError
 import sys
 import threading
 
@@ -129,6 +131,18 @@ class IrMailServer(models.Model):
             except UserError as e:
                 # let UserErrors (messages) bubble up
                 raise e
+            except UnicodeError as e:
+                raise UserError(_("Invalid server name !\n %s", ustr(e)))
+            except (gaierror, timeout) as e:
+                raise UserError(_("No response received. Check server address and port number.\n %s", ustr(e)))
+            except smtplib.SMTPServerDisconnected as e:
+                raise UserError(_("The server has closed the connection unexpectedly. Check configuration served on this port number.\n %s", ustr(e.strerror)))
+            except smtplib.SMTPResponseException as e:
+                raise UserError(_("Server replied with following exception:\n %s", ustr(e.smtp_error)))
+            except smtplib.SMTPException as e:
+                raise UserError(_("An SMTP exception occurred. Check port number and connection security type.\n %s", ustr(e.smtp_error)))
+            except SSLError as e:
+                raise UserError(_("An SSL exception occurred. Check connection security type.\n %s", ustr(e)))
             except Exception as e:
                 raise UserError(_("Connection Test Failed! Here is what we got instead:\n %s", ustr(e)))
             finally: