Updating email guide

2 files changed, 85 insertions, 14 deletions

diff --git a/doc/install/SMTP-Email-Setup.md b/doc/install/SMTP-Email-Setup.md
index 4e06d2f99..2100130ee 100644
--- a/doc/install/SMTP-Email-Setup.md
+++ b/doc/install/SMTP-Email-Setup.md
@@ -14,6 +14,7 @@ To enable email, configure an SMTP email service as follows:
 	         3. Copy the `Server Name`, `Port`, `SMTP Username`, and `SMTP Password` for Step 2 below. 
 	         4. From the `Domains` menu set up and verify a new domain, then enable `Generate DKIM Settings` for the domain.
 	         5. Choose an sender address like `mattermost@example.com` and click `Send a Test Email` to verify setup is working correctly. 
+
 2.  **Configure SMTP settings** 
 	1.  Open the **System Console** by logging into an existing team and accessing "System Console" from the main menu.
 	     1.  Alternatively, if a team doesn't yet exist, go to `http://dockerhost:8065/` in your browser, create a team, then from the main menu click **System Console**
@@ -29,15 +30,42 @@ To enable email, configure an SMTP email service as follows:
 	       9. **SMTP Port**: `SMTP Port` from Step 1
 	       10. **Connection Security**: `TLS (Recommended)`
 	       11. Then click **Save**
+	       12. Then click **Test Connection**
+	       13. If the test failed please look in **OTHER** > **Logs** for any errors that look like `[EROR] /api/v1/admin/test_email ...`
+
+### Known Good Sample Settings
+
+##### Amazon SES
+* Set **SMTP Username** to **AKIASKLDSKDIWEOWE**
+* Set **SMTP Password** to **AdskfjAKLSDJShflsdfjkakldADkjkjdfKAJDSlkjweiqQIWEOU**
+* Set **SMTP Server** to **email-smtp.us-east-1.amazonaws.com**
+* Set **SMTP Port** to **465**
+* Set **Connection Security** to **TLS**
+
+##### Postfix
+* Make sure Postfix is installed on the machine where Mattermost is installed
+* Set **SMTP Username** to **<empty>**
+* Set **SMTP Password** to **<empty>**
+* Set **SMTP Server** to **localhost**
+* Set **SMTP Port** to **25**
+* Set **Connection Security** to **<empty>**
+
+##### Gmail
+* Information needed
+
+##### Office 365
+* Information needed
+
+##### Hotmail
+* Information needed
 
-3.  **Restart Mattermost**
-	1. Use `ps -A`  to find the process ID ("pid") for service named `platform` and stop it using `kill [pid]`
-	2. The service should restart automatically. Run `ps -A` to verify the `platform` is running again 
-	3. Use the reset password page (E.g. _example.com/teamname/reset_password_) to test that email is now working by entering your email and clicking **Reset my password**.
-	4. Note: The next time users log out, or when their session tokens expire, each will be required to verify their email address.
 
 ### Troubleshooting SMTP
 
+#### Tip 1
+If you fill in **SMTP Username** and **SMTP Password** then you must set **Connection Security** to **TLS** or to **STARTTLS**
+
+#### Tip 2
 If you have issues with your SMTP install, from your Mattermost team site go to the main menu and open **System Console -> Logs** to look for error messages related to your setup. You can do a search for the error code to narrow down the issue. Sometimes ISPs require nuanced setups for SMTP and error codes can hint at how to make the proper adjustments. 
 
 For example, if **System Console -> Logs** has an error code reading: 
@@ -48,4 +76,19 @@ Connection unsuccessful: Failed to add to email address - 554 5.7.1 <unknown[IP-
 
 Search for `554 5.7.1 error` and `Client host rejected: Access denied`.
 
-
+#### Tip 3
+* Attempt to telnet to the email service to make sure the server is reachable.
+* You must run the following commands from the same machine or virtual instance where `mattermost/bin/platform` is located.  So if you're running Mattermost from docker you need to `docker exec -ti mattermost-dev /bin/bash`
+* Telnet into email server with `telnet mail.example.com 25`.  If the command works you should see something like
+```
+Trying 24.121.12.143...
+Connected to mail.example.com.
+220 mail.example.com NO UCE ESMTP
+```
+* Then type something like `HELO <your mail server domain>`.  If the command works you should see something like
+```
+250-mail.example.com NO UCE
+250-STARTTLS
+250-PIPELINING
+250 8BITMIME
+```
\ No newline at end of file
diff --git a/doc/install/Troubleshooting-Email.md b/doc/install/Troubleshooting-Email.md
index 0ddc807bb..b8e34de25 100644
--- a/doc/install/Troubleshooting-Email.md
+++ b/doc/install/Troubleshooting-Email.md
@@ -1,14 +1,42 @@
+### Mattermost Email Troubleshooting
 
-change settings via system console
+#### Update Email Settings in System Console
+* Login to Mattermost with an account that has the `system admin` role
+* Open the System Console by clicking on **...** > **System Console** > **Email Settings*
+    * Change **Send Email Notifications** to **true**
+    * Change **Require Email Verification** to **true**
+* Set **Notification Email Address** must be set and must be a valid email allowed as the **FROM** field on the email server.  Some email servers will only allow certian accounts to send emails.
+* Set the **SMTP** fields based on your email service.  Some known good samples are listed below.
+* If you fill in **SMTP Username** and **SMTP Password** then you must set **Connection Security** to **TLS** or to **STARTTLS**
+* Once you've filled in all the information please make sure to **Test Connection**
+* If the test failed please look in **OTHER** > **Logs** for any errors that look like `[EROR] /api/v1/admin/test_email ...`
 
-known good settings for providers:
-amazon ses
-postfix
-gmail
-hotmail
-sendgrid
+#### Known Good Sample Settings
+
+##### Amazon SES
+* Set **SMTP Username** to **AKIASKLDSKDIWEOWE**
+* Set **SMTP Password** to **AdskfjAKLSDJShflsdfjkakldADkjkjdfKAJDSlkjweiqQIWEOU**
+* Set **SMTP Server** to **email-smtp.us-east-1.amazonaws.com**
+* Set **SMTP Port** to **465**
+* Set **Connection Security** to **TLS**
+
+##### Postfix
+* Make sure Postfix is installed on the machine where Mattermost is installed
+* Set **SMTP Username** to **<empty>**
+* Set **SMTP Password** to **<empty>**
+* Set **SMTP Server** to **localhost**
+* Set **SMTP Port** to **25**
+* Set **Connection Security** to **<empty>**
+
+##### Gmail
+* Information needed
+
+##### Office 365
+* Information needed
+
+##### Hotmail
+* Information needed
 
-if you fill in a username/password you must use a secure connection like TLS or STARTTLS
 
 test connection
 check error logs