>>>Hi,
>>>
>>>I am trying to send email using GMAIL server. For SMTP I use "smtp.gmail.com", port 465, and then user gmail user ID and password.
>>>But I get a message "cannot connect to the server"
>>>Is there a setting or something I am missing?
>>
>>In your mail client you need to specify that encryption is required: https://www.lifewire.com/what-are-the-gmail-smtp-settings-1170854
>>
>>If you're using port 465, specify the encryption type is SSL. If you use TLS it's port 587.
>>
>>Also make sure your user name is not just "YourUserName", instead it has to be "YourUserName@gmail.com".
>>
>>Whichever port you use, you need to make sure your environment allows outgoing traffic on that port. That's not usually an issue in small environments (typically no restrictions on outgoing traffic) but if it's been locked down for any reason then you'll need to get the sysadmin to allow your traffic.
>
>First, thank you. I am using West-Wind wwipstuff for sending email from my VFP application. And I am not sure there is an option to specify SSL or TLS. So maybe using this tool emailing through gmail is not possible. I will double check.

I have had some success in sending E-mail through gmail in the past (and this was an application that was using raw socket connections established through direct API calls) -- though I've not done so in a while. A number of years ago Google started tightening up the security, which might be related to the problem you're encountering. One setting you may have to change in the gmail account is the "allow less secure software access" (or something worded something like it) setting. Around the same time I'd noticed that the Windows Live Mail would not connect unless this setting was configured to "allow". One annoying bit is that this setting would eventually get reset to the more secure configuration after a while, and as a result would have to go to the Website, reset a few items. Usually by this time you may have had enough failed connection that you have to use recovery options to unlock the account and regain access --- nothing difficult or overly time-consuming -- just bothersome.