Issue #9627 has been reported by Josh Goebel.

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Bug #9627: SMTP does not properly dot-stuff an unterminated last line
https://bugs.ruby-lang.org/issues/9627

* Author: Josh Goebel
* Status: Open
* Priority: Normal
* Assignee: 
* Category: lib
* Target version: 
* ruby -v: ruby 1.9.3p448 (2013-06-27 revision 41675) [x86_64-linux]
* Backport: 1.9.3: UNKNOWN, 2.0.0: UNKNOWN, 2.1: UNKNOWN
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```
str = "Date: Wed, 12 Mar 2014 16:02:26 -0400\r\nFrom: someone / aol.com\r\nTo: someone / aol.com\r\nMessage-ID: <5320bd52be4d3_6d653fd3d8c339e458df / Joshs-MacBook-Pro.local.mail>\r\nMime-Version: 1.0\r\nContent-Type: text/plain;\r\n charset=UTF-8\r\nContent-Transfer-Encoding: 7bit\r\n\r\nlook, a period with no endline\r\n."

      smtp = Net::SMTP.new(...)
      smtp.start(...) do |smtp_obj|
        response = smtp_obj.sendmail(message, "someone / aol.com","someone / aol.com")
      end
```

The SMTP server is going to throw a 400 or 500 error (depending on it's configuration) because the last period is send un-stuffed in the DATA block:

```
look, a period with no endline
.
.
```

When it should be:

```
look, a period with no end line
..
.

```

(ie, not dot-stuffed) and the second period the SMTP server doesn't know what to do with.  Adding an additional new-line fixes the problem, but I the in-line documentation for SMTP send_message does not say anything about a new-line being requires for message sending to work.

Sorry, I can't test against the latest Ruby right now, but this is confirmed against 1.9.3 r448.  If someone can confirm against newer that would be great.

I did do a search for "SMTP" and did not see this reported anywhere in the Issues database.

I had originally filed a pull request against Mail: https://github.com/mikel/mail/pull/683



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