In case anyone has the same problem in the future and finds this post, the 
problem was with a failure to enclose parentheses in the address in quotes. 
For example, this input caused a parse error for the Mail gem:

"Allison (Allie) Doe <[email protected]>"

and the fix was changing it to:

"\"Allison (Allie) Doe\" <[email protected]>"

On Sunday, December 11, 2016 at 3:55:18 PM UTC-5, Jon Bauman wrote:
>
> I write an administer a web app for a non-profit which runs on the free 
> level of Heroku's service since they don't have the budget for more.
>
> One of the features they need is a way to send emails to all ~300 
> volunteers to make announcements. To protect volunteer privacy, my approach 
> was to implement these announcements via BCC addressing. However, I ran 
> into something strange: when sending the emails with Rails' ActionMailer 
> via SendGrid, the addresses were left intact in the BCC header received by 
> recipients; something I've never seen before. I followed up with SendGrid 
> support and their response was to use their (SendGrid-specific) API. I'd 
> rather keep using ActionMailer since it makes it easier to switch email 
> addons (which I've had to to once already when Mandrill discontinued their 
> free level).
>
> Any thoughts about what might be going on here, or suggestions for Heroku 
> email addons which work correctly with BCC addressing via ActionMailer?
>

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