Answers.Body: <p>There's an administrative setting that controls that limit here:</p>
  
  <p>Administer -> System Settings -> Misc (Undelete, PDFs, Limits, Logging, Captcha, etc.)</p>
  
  <p>The "syntax error" you are seeing is likely what the Civi mailer is getting back from the smtp server. I've seen that as a kind of catchall error message from mailers (e.g. it's what sparkpost will report when not configured). I don't think that Civi can do anything other than pass it on - i.e. the reporting error is from the system that's trying/failing to send out the mail.</p>
  
  <p>Personally, I think there should be a message in the CiviMail system strongly discouraging attachments and encouraging attachments to be uploaded and linked to instead. That will increase deliverability.</p>
  
  <p>The only really good use-case for attachments is if the document is private.</p>
  
  <p>So the answer to your question is: "no".</p>
  
Answers.ContentLicense: CC BY-SA 4.0
Answers.CreationDate: 2019-12-16T02:42:21.753Z
Answers.Text: While I agree with the sentiments, it's not real world, no matter how hard I fight it.  Additionally, while helpful in the overall theme, this doesn't answer the question.  Sorry.
Answers.UserDisplayName: G H
Answers.ContentLicense: CC BY-SA 4.0
Answers.CreationDate: 2019-12-16T15:37:06.000Z
Answers.Text: Perhaps you want to submit an extension or PR with a warning or message when using attachments in a CiviMail? To the effect that it's a bad idea and it might fail with a misleading error message from the mailer?
Answers.UserDisplayName: Alan Dixon
Answers.ContentLicense: CC BY-SA 4.0
Answers.CreationDate: 2019-12-19T14:01:38.307Z
Answers.Text: Great idea, if it doesn't already exist.  However, this still is not on the topic of CiviCRM's bounce processing throwing an error/message when something like this happens.
Answers.UserDisplayName: G H
Answers.ContentLicense: CC BY-SA 4.0
Answers.CreationDate: 2019-12-20T15:39:13.800Z
Answers.Text: But you did see the update to my answer that is specific to your question, yes?
Answers.UserDisplayName: Alan Dixon
Answers.ContentLicense: CC BY-SA 4.0
Answers.CreationDate: 2019-12-06T19:51:21.513Z
Answers.LastActivityDate: 2019-12-16T15:34:55.667Z
Answers.LastEditDate: 2019-12-16T15:34:55.667Z
Answers.UserDisplayName: Alan Dixon
Body: <p>Recently had a user attach a .docx file that was 14 MB to a mailing.  (Probably a single picture in the document was to blame.)  As one would expect, the messages bounced rather than being delivered.  However, the mailing reports just showed a bounce type of Syntax.  As you can imagine, this is rather unhelpful.  Digging around, I finally turned to the system's logging for maillog where I found the report of the attachment too large.  Should I have found this information somewhere in CiviCRM itself?  Perhaps in the mailing report that I overlooked?</p>
  
Comments.ContentLicense: CC BY-SA 4.0
Comments.CreationDate: 2019-12-16T18:46:08.170Z
Comments.Text: Did you send a test e-mail to yourself first? Always a good idea. 14MB is pretty huge for an attachment - I believe Outlook/Exchange will often not allow receiving attachments larger than 10MB, for example. Also the fact that it's a .docx and could contain malware, like a Word macro, would probably cause many receiving systems to block it.
Comments.UserDisplayName: Joe McLaughlin
Comments.ContentLicense: CC BY-SA 4.0
Comments.CreationDate: 2019-12-19T13:58:41.543Z
Comments.Text: Yep.  Again, you are correct.  Those are all real problems that users are really good at not knowing, not remembering, and ignoring.
Comments.UserDisplayName: G H
Comments.ContentLicense: CC BY-SA 4.0
Comments.CreationDate: 2019-12-20T18:05:12.383Z
Comments.Text: OK then for now my suggested real world solution is to require a test e-mail be sent via permissions :) . And I agree that there should be a warning that an attachment is (probably) too large, added in core.
Comments.UserDisplayName: Joe McLaughlin
Tags: <civimail><civireport><logging>
Title: Attachment too large for mailing - should there have been a warning?
ThreadText: # Attachment too large for mailing - should there have been a warning?
  
  (Asked by: username_0 on 2019-12-04)
  
  Recently had a user attach a .docx file that was 14 MB to a mailing. (Probably a single picture in the document was to blame.) As one would expect, the messages bounced rather than being delivered. However, the mailing reports just showed a bounce type of Syntax. As you can imagine, this is rather unhelpful. Digging around, I finally turned to the system's logging for maillog where I found the report of the attachment too large. Should I have found this information somewhere in CiviCRM itself? Perhaps in the mailing report that I overlooked?
  
  **Tags:** civimail, civireport, logging
  
  > **Comments:**
  > **username_1**: Did you send a test e-mail to yourself first? Always a good idea. 14MB is pretty huge for an attachment - I believe Outlook/Exchange will often not allow receiving attachments larger than 10MB, for example. Also the fact that it's a .docx and could contain malware, like a Word macro, would probably cause many receiving systems to block it.  
  > **username_0**: Yep.  Again, you are correct.  Those are all real problems that users are really good at not knowing, not remembering, and ignoring.  
  > **username_1**: OK then for now my suggested real world solution is to require a test e-mail be sent via permissions :) . And I agree that there should be a warning that an attachment is (probably) too large, added in core.  
  
  ---
  
  ## 1 answers
  
  ### Answer by username_2 on 2019-12-06. Score: 1 | Accepted answer
  
  There's an administrative setting that controls that limit here:
  
  Administer -> System Settings -> Misc (Undelete, PDFs, Limits, Logging, Captcha, etc.)
  
  The "syntax error" you are seeing is likely what the Civi mailer is getting back from the smtp server. I've seen that as a kind of catchall error message from mailers (e.g. it's what sparkpost will report when not configured). I don't think that Civi can do anything other than pass it on - i.e. the reporting error is from the system that's trying/failing to send out the mail.
  
  Personally, I think there should be a message in the CiviMail system strongly discouraging attachments and encouraging attachments to be uploaded and linked to instead. That will increase deliverability.
  
  The only really good use-case for attachments is if the document is private.
  
  So the answer to your question is: "no".
  
  > **Comments:**
  > **username_0**: While I agree with the sentiments, it's not real world, no matter how hard I fight it.  Additionally, while helpful in the overall theme, this doesn't answer the question.  Sorry.  
  > **username_2**: Perhaps you want to submit an extension or PR with a warning or message when using attachments in a CiviMail? To the effect that it's a bad idea and it might fail with a misleading error message from the mailer?  
  > **username_0**: Great idea, if it doesn't already exist.  However, this still is not on the topic of CiviCRM's bounce processing throwing an error/message when something like this happens.  
  > **username_2**: But you did see the update to my answer that is specific to your question, yes?  
  
  ---
  
  