### Author:  [@Kristian](https://meta.discourse.org/u/Kristian)
#### Post date: [April 30, 2020, 9:24am UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/1 "2020-04-30T09:24:22Z")
My digitalocean discourse droplet can’t send mails. The error I get is:
```
Delivered mail d8f9bf03-a3ce-4b42-8226-fc4f40a9c724@foo.barbar.com (5099.4ms)
Job exception: 504 5.7.4 Unrecognized authentication type [BL0PR0102CA0036.prod.exchangelabs.com]
```
My settings are:
```
DISCOURSE_SMTP_ADDRESS: smtp.office365.com
DISCOURSE_SMTP_PORT: 587
DISCOURSE_SMTP_USER_NAME: foo@bar.com
DISCOURSE_SMTP_PASSWORD: "mypassword"
DISCOURSE_SMTP_ENABLE_START_TLS: true # (optional, default true)
```
I have tried telnet from the droplet and it gives no errors:
`telnet smtp.office365.com 587`
What could be the problem? I have tried the smtp settings combination locally from python and it works so I assume that’s not the problem.
---
### Author:  [@mik](https://meta.discourse.org/u/mik)
#### Post date: [April 30, 2020, 10:34am UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/2 "2020-04-30T10:34:59Z")
Hi,
Try to add:
```
DISCOURSE_SMTP_AUTHENTICATION: login
```
And at end of app.yml:
```
- exec: rails r "SiteSetting.notification_email='foo@bar.com'"`
```
---
### Author:  [@Kristian](https://meta.discourse.org/u/Kristian)
#### Post date: [April 30, 2020, 11:27am UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/3 "2020-04-30T11:27:38Z")
Hi mik
The exec statement fails:
```
FAILED
--------------------
Pups::ExecError: rails r "SiteSetting.notification_email='foo@bar.com'"` failed with return #
Location of failure: /pups/lib/pups/exec_command.rb:112:in `spawn'
exec failed with the params "rails r \"SiteSetting.notification_email='foo@bar.com'\"`"
9628e31c775b74ad0f3a555b6af27701aa40b1f8b86419fa44a7c389cc5e34ae
**FAILED TO BOOTSTRAP** please scroll up and look for earlier error messages, there may be more than one.
./discourse-doctor may help diagnose the problem.
```
---
### Author:  [@Kristian](https://meta.discourse.org/u/Kristian)
#### Post date: [April 30, 2020, 12:28pm UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/4 "2020-04-30T12:28:49Z")
Update leaving out the exec command but adding:
```plaintext
DISCOURSE_SMTP_AUTHENTICATION: login
```
does not produce return an error I only get:
`Delivered mail be6d8718-5445-48cc-a120-6d6d1eab9eb7@discourse.bar.com (4307.2ms)`
But I still don’t get an email in my inbox (I checked the spam folder)
---
### Author:  [@mik](https://meta.discourse.org/u/mik)
#### Post date: [April 30, 2020, 1:34pm UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/5 "2020-04-30T13:34:09Z")
You can try this in order to try to find the good configuration and perhaps have some error message:
```
docker exec -t -i id_of_your_container /bin/bash
```
Then inside the container:
```
apt install s-nail
echo "This is the message body and contains the message" | s-nail -r "foo@bar.com" -s mysubject -S "smtp=smtp.office365.com:587" -S smtp-use-starttls -S smtp-auth=login -S smtp-auth-user="foo@bar.com" -S smtp-auth-password="xxxxxxxx" -S ssl-verify=ignore youremail@example.com
```
You can change the different value (ie : smtp-auth=login ) to try to find the good one. And perhaps you will have more precise error message.
---
### Author:  [@Kristian](https://meta.discourse.org/u/Kristian)
#### Post date: [April 30, 2020, 3:01pm UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/6 "2020-04-30T15:01:54Z")
```plaintext
echo "This is the message body and contains the message" | s-nail -r "foo@bar.com" -s mysubject -S "smtp=smtp.office365.com:587" -S smtp-use-starttls -S smtp-auth=login -S smtp-auth-user="foo@bar.com" -S smtp-auth-password="xxxxxxxx" -S ssl-verify=ignore youremail@example.com
```
This worked and I got the mail! I had to change the smtp-auth-password=“xxxxxxxx” to single quotes though since my password starts with an ‘!’.
The only difference I can see to my config is this flag:
-S ssl-verify=ignore
Do I have to add that too?
Thanks for your help!
---
### Author:  [@mik](https://meta.discourse.org/u/mik)
#### Post date: [April 30, 2020, 3:14pm UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/7 "2020-04-30T15:14:31Z")
Try to add:
```plaintext
DISCOURSE_SMTP_OPENSSL_VERIFY_MODE: none
```
In your config, it is the same as ssl-verify=ignore .
---
### Author:  [@Kristian](https://meta.discourse.org/u/Kristian)
#### Post date: [April 30, 2020, 3:59pm UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/8 "2020-04-30T15:59:39Z")
No errors but still no email in the inbox ☹ To recap, this is my config now:
```
DISCOURSE_SMTP_ADDRESS: smtp.office365.com
DISCOURSE_SMTP_PORT: 587
DISCOURSE_SMTP_USER_NAME: info@foo.com
DISCOURSE_SMTP_PASSWORD: 'xxx'
DISCOURSE_SMTP_ENABLE_START_TLS: true # (optional, default true)
DISCOURSE_SMTP_AUTHENTICATION: login
DISCOURSE_SMTP_OPENSSL_VERIFY_MODE: none
```
---
### Author:  [@mik](https://meta.discourse.org/u/mik)
#### Post date: [April 30, 2020, 4:31pm UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/9 "2020-04-30T16:31:35Z")
Please try to add this again (it is the _same_ as “-r” option in the s-nail command line test :
```
- exec: rails r "SiteSetting.notification_email='foo@bar.com'"`
```
The email must be the same as your account.
And check the indentation in the file app.yml, and do not forget the “-” at the beginning. There is 2 space then the “-” then a space then “exec…” 🙂
---
### Author:  [@Capstan](https://meta.discourse.org/u/Capstan)
#### Post date: [May 3, 2020, 1:34am UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/10 "2020-05-03T01:34:48Z")
I’m having this problem also. I spun up a droplet with Discourse on Digital Ocean as well. I used the “sudo ./discourse-doctor” command after trying all of these suggestions and rebuilding each time ( sudo ./launcher rebuild app).
`504 5.7.4 Unrecognized authentication type [BL0PR01CA0015.prod.exchangelabs.com]`
s-nail from within the container did work for me also, no problem. And I tried it without the “-S ssl-verify=ignore” clause, worked fine. Can someone verify that what gets installed on the digital ocean droplet does send email correctly?
---
### Author:  [@riking](https://meta.discourse.org/u/riking)
#### Post date: [May 3, 2020, 6:32am UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/12 "2020-05-03T06:32:27Z")
Find out from your mail admins what the valid values of `smtp_authentication` are, and set DISCOURSE\_SMTP\_AUTHENTICATION to one that works.
---
### Author:  [@Kristian](https://meta.discourse.org/u/Kristian)
#### Post date: [May 3, 2020, 9:14am UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/13 "2020-05-03T09:14:52Z")
Thanks for all the help, I have given up and switched to another forum solution.
---
### Author:  [@Capstan](https://meta.discourse.org/u/Capstan)
#### Post date: [May 3, 2020, 2:38pm UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/14 "2020-05-03T14:38:44Z")
It is Microsoft, their instructions are as follows, no `smtp_authentication` is specified;
- SMTP server name [smtp.office365.com](http://smtp.office365.com)
- SMTP port 587
- SMTP encryption method STARTTLS
Do you not support this kind of server? Can you simply make an account, connect to it, and tell us what the settings should be?
---
### Author:  [@m.jason.miller](https://meta.discourse.org/u/m.jason.miller)
#### Post date: [August 9, 2021, 5:46pm UTC](https://meta.discourse.org/t/sending-emails-not-working/149883/15 "2021-08-09T17:46:49Z")
`DISCOURSE_SMTP_OPENSSL_VERIFY_MODE: none`
This solved _my_ issue thanks!