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| - |`--email-force-tls`|`CODER_EMAIL_FORCE_TLS`|`bool`| Force a TLS connection to the configured SMTP smarthost. If port 465 is used, TLS will be forced. See https://datatracker.ietf.org/doc/html/rfc8314#section-3.3.| false |
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| - |`--email-tls-starttls`|`CODER_EMAIL_TLS_STARTTLS`|`bool`| Enable STARTTLS to upgrade insecure SMTP connections using TLS. Ignored if `CODER_NOTIFICATIONS_EMAIL_FORCE_TLS` is set. | false |
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| - |`--email-tls-skip-verify`|`CODER_EMAIL_TLS_SKIPVERIFY`|`bool`| Skip verification of the target server's certificate (**insecure**). | false |
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| - |`--email-tls-server-name`|`CODER_EMAIL_TLS_SERVERNAME`|`string`| Server name to verify against the target certificate. ||
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| - |`--email-tls-cert-file`|`CODER_EMAIL_TLS_CERTFILE`|`string`| Certificate file to use. ||
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| - |`--email-tls-cert-key-file`|`CODER_EMAIL_TLS_CERTKEYFILE`|`string`| Certificate key file to use. ||
| - |`--email-force-tls`|`CODER_EMAIL_FORCE_TLS`|`bool`| Force a TLS connection to the configured SMTP smarthost. If port 465 is used, TLS will be forced. See <https://datatracker.ietf.org/doc/html/rfc8314#section-3.3>. | false |
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| - |`--email-tls-starttls`|`CODER_EMAIL_TLS_STARTTLS`|`bool`| Enable STARTTLS to upgrade insecure SMTP connections using TLS. Ignored if `CODER_NOTIFICATIONS_EMAIL_FORCE_TLS` is set. | false |
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| - |`--email-tls-skip-verify`|`CODER_EMAIL_TLS_SKIPVERIFY`|`bool`| Skip verification of the target server's certificate (**insecure**). | false |
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| - |`--email-tls-server-name`|`CODER_EMAIL_TLS_SERVERNAME`|`string`| Server name to verify against the target certificate. ||
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| - |`--email-tls-cert-file`|`CODER_EMAIL_TLS_CERTFILE`|`string`| Certificate file to use. ||
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| - |`--email-tls-cert-key-file`|`CODER_EMAIL_TLS_CERTKEYFILE`|`string`| Certificate key file to use. ||
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**NOTE:** you _MUST_ use `CODER_EMAIL_FORCE_TLS` if your smarthost supports TLS
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on a port other than `465`.
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After setting the required fields above:
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1. Create an [App Password](https://myaccount.google.com/apppasswords) using the
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account you wish to send from
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2. Set the following configuration options:
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```
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account you wish to send from.
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1. Set the following configuration options:
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```text
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CODER_EMAIL_SMARTHOST=smtp.gmail.com:465
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CODER_EMAIL_AUTH_USERNAME=<user>@<domain>
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CODER_EMAIL_AUTH_PASSWORD="<app password created above>"
@@ -141,8 +143,9 @@ for more options.
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After setting the required fields above:
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1. Setup an account on Microsoft 365 or outlook.com
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