#33498: Email TO: field unusual behavior of changing the input, can lead to 
errors
-----------------------------------------+------------------------
               Reporter:  Michael        |          Owner:  nobody
                   Type:  Uncategorized  |         Status:  new
              Component:  Core (Mail)    |        Version:  4.0
               Severity:  Normal         |       Keywords:  email
           Triage Stage:  Unreviewed     |      Has patch:  0
    Needs documentation:  0              |    Needs tests:  0
Patch needs improvement:  0              |  Easy pickings:  0
                  UI/UX:  0              |
-----------------------------------------+------------------------
 This code will generate a 500 error instead of sending an email about the
 404 error (the problem is the TO field). It's a hard to error to find due
 to no stack trace, had to binary search a lot of code to find it (cause it
 works fine with console email backend (i.e during dev)):

 {{{
     from django.core.mail import send_mail

     send_mail(
         f'Suspicious file requested from {client_ip} for {path}',
         f'Suspicious file requested from {client_ip}.\nURL:
 {absolute_url}',
         '"Notifications" <[email protected]>',
         [Cfg.EMAIL_SUPPORT],
         fail_silently=True,
     )
 }}}

 If one emoves the double quotes:
 {{{
     send_mail(
         f'Suspicious file requested from {client_ip} for {path}',
         f'Suspicious file requested from {client_ip}.\nURL:
 {absolute_url}',
         'Notifications <[email protected]>',
         [Cfg.EMAIL_SUPPORT],
         fail_silently=True,
     )
 }}}

 Then the from field in gmail is:
 {{{
         'Notifications' via support <[email protected]>
 }}}

 Which is not what it was set to. The person's name was set to
 `Notifications` not `'Notifications' via support`, and the from email
 address was set to `[email protected]` not `[email protected]`

 This is my settings.py:
 {{{
 SERVER_EMAIL = f'[email protected]'  # The reply to
 DEFAULT_FROM_EMAIL = [email protected]'
 ADMINS = [('Support', '[email protected]')]
 MANAGERS = ADMINS
 EMAIL_SUBJECT_PREFIX = "Example Server: "
 }}}

 THe documentation says:
 {{{
 from_email: A string. If None, Django will use the value of the
 DEFAULT_FROM_EMAIL setting.
 }}}
 It does not specify this unusual behavior.

-- 
Ticket URL: <https://code.djangoproject.com/ticket/33498>
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