You can use mailgun.com to get this working pretty simply and it's free for 
under 10,000 emails.

On Wednesday, December 21, 2016 at 3:37:59 AM UTC-5, Harvey Zhang wrote:
>
> What if I have to use a Socks5(127.0.0.1:1080) or http(127.0.0.1:8118) 
> proxy to connect to gmail?
> How should stunnel be configured?
>
>
> On Friday, December 4, 2009 at 4:32:13 PM UTC+8, Andrey Tkachuk (MLO) 
> wrote:
>>
>> In response to this message about using Gmail  for sending MLO 
>> reminder emails: 
>>
>> http://groups.google.com/group/mylifeorganized/browse_thread/thread/ae0449b740adbc9e/
>>  
>>
>> qhamel just sent me more detailed instructions (Thanks qhamel!) : 
>>
>> ------------------------ 
>> Here is a more detailed explanation on how to configure use MLO with 
>> Gmail: 
>>
>> GMail as your SMTP server 
>>
>> GMail requires secure connections 
>>
>> If you want to configure MLO to use GMail as its SMTP server, you will 
>> find that currently MLO does not support secure (TLS/STARTTLS) 
>> connections for email. To work around this, you will need to run 
>> another program (stunnel) to "wrap" MLO's connection to GMail. MLO 
>> will then connect to stunnel, which will connect to gmail. 
>>
>> Download / Configure stunnel 
>> Download the latest windows Stunnell installer and run the installer. 
>> Install stunnel to the directory C:\Stunnel. 
>>
>> Inside the c:\Stunnel directory create a text file called 
>> gmailsmtp.txt with the following content (8 lines). 
>>
>> ; SMTP configuration for Gmail 
>> output = SMTPgmail.log 
>> taskbar = no 
>> cert = stunnel.pem 
>> client = yes 
>> [ssmtp] 
>> accept = 10.0.0.1:8025 
>> connect = smtp.gmail.com:465 
>>
>> Change 10.0.0.1 to your computer's IP address or name. Do not use 
>> "localhost" or 127.0.0.1 as that won't work. The best way is to go to 
>> Control Panel and click on "System" and click on the Computer name 
>> tab. Highlight and copy the full computer name for your PC. 
>>
>> Open a command prompt (cmd.exe) and navigate to the stunnel install 
>> directory (CD C:\Stunnel). Enter the following 2 commands to run 
>> stunnel as a Windows Service: 
>>
>> stunnel -install gmailsmtp.txt 
>> net start stunnel 
>>
>> Now Configure MLO email settings 
>>
>> Now you need to configure MLO Email Settings to connect to stunnel. 
>>
>> Your SMTP server: Your computer name you just got off of the computer 
>> name tab 
>> Port: 8025 
>> Check My server requires Authentication 
>> Userid: your gmail address (joh...@gmail.com) 
>> Password: your gmail password 
>> Now press the "Test" button. If you configured everything correctly, a 
>> test email will be sent. This test email will also show up inside your 
>> gmail account in the "Sent Mail" folder. 
>>
>> qhamel 
>> ------------- 
>>
>

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