diff --git a/lib/smtp.c b/lib/smtp.c
index d9f1a854aa..3f3b45a954 100644
--- a/lib/smtp.c
+++ b/lib/smtp.c
@@ -1289,6 +1289,11 @@ static CURLcode smtp_perform(struct connectdata *conn, bool *connected,
   /* Store the first recipient (or NULL if not specified) */
   smtp->rcpt = data->set.mail_rcpt;
 
+  /* Initial data character is the first character in line: it is implicitly
+     preceded by a virtual CRLF. */
+  smtp->trailing_crlf = TRUE;
+  smtp->eob = 2;
+
   /* Start the first command in the DO phase */
   if((data->set.upload || data->set.mimepost.kind) && data->set.mail_rcpt)
     /* MAIL transfer */
diff --git a/tests/data/Makefile.inc b/tests/data/Makefile.inc
index 9635d12a1f..31d2999428 100644
--- a/tests/data/Makefile.inc
+++ b/tests/data/Makefile.inc
@@ -103,7 +103,7 @@ test909 test910 test911 test912 test913 test914 test915 test916 test917 \
 test918 test919 test920 test921 test922 test923 test924 test925 test926 \
 test927 test928 test929 test930 test931 test932 test933 test934 test935 \
 test936 test937 test938 test939 test940 test941 test942 test943 test944 \
-test945 test946 test947 test948 test949 test950 \
+test945 test946 test947 test948 test949 test950 test951 test952 \
 \
 test1000 test1001 test1002 test1003 test1004 test1005 test1006 test1007 \
 test1008 test1009 test1010 test1011 test1012 test1013 test1014 test1015 \
diff --git a/tests/data/test911 b/tests/data/test911
index cc87349b89..f4c545830f 100644
--- a/tests/data/test911
+++ b/tests/data/test911
@@ -40,7 +40,6 @@ DATA
 QUIT
 </protocol>
 <upload>
-
 .
 </upload>
 </verify>
diff --git a/tests/data/test951 b/tests/data/test951
new file mode 100644
index 0000000000..7d2e17b1be
--- /dev/null
+++ b/tests/data/test951
@@ -0,0 +1,45 @@
+<testcase>
+<info>
+<keywords>
+SMTP
+</keywords>
+</info>
+
+#
+# Server-side
+<reply>
+</reply>
+
+#
+# Client-side
+<client>
+<server>
+smtp
+</server>
+ <name>
+SMTP data with dot as first character
+ </name>
+<stdin>
+.This first line starts with a dot
+</stdin>
+<command>
+smtp://%HOSTIP:%SMTPPORT/951 --mail-rcpt recipient@example.com --mail-from sender@example.com -T -
+</command>
+</client>
+
+#
+# Verify data after the test has been "shot"
+<verify>
+<protocol>
+EHLO 951
+MAIL FROM:<sender@example.com>
+RCPT TO:<recipient@example.com>
+DATA
+QUIT
+</protocol>
+<upload>
+..This first line starts with a dot
+.
+</upload>
+</verify>
+</testcase>
diff --git a/tests/data/test952 b/tests/data/test952
new file mode 100644
index 0000000000..54334b21ef
--- /dev/null
+++ b/tests/data/test952
@@ -0,0 +1,45 @@
+<testcase>
+<info>
+<keywords>
+SMTP
+</keywords>
+</info>
+
+#
+# Server-side
+<reply>
+</reply>
+
+#
+# Client-side
+<client>
+<server>
+smtp
+</server>
+ <name>
+SMTP data with single dot-only line
+ </name>
+<stdin>
+.
+</stdin>
+<command>
+smtp://%HOSTIP:%SMTPPORT/952 --mail-rcpt recipient@example.com --mail-from sender@example.com -T -
+</command>
+</client>
+
+#
+# Verify data after the test has been "shot"
+<verify>
+<protocol>
+EHLO 952
+MAIL FROM:<sender@example.com>
+RCPT TO:<recipient@example.com>
+DATA
+QUIT
+</protocol>
+<upload>
+..
+.
+</upload>
+</verify>
+</testcase>
diff --git a/tests/ftpserver.pl b/tests/ftpserver.pl
index 956275881d..f7f4fa2ae3 100755
--- a/tests/ftpserver.pl
+++ b/tests/ftpserver.pl
@@ -6,7 +6,7 @@
 #                            | (__| |_| |  _ <| |___
 #                             \___|\___/|_| \_\_____|
 #
-# Copyright (C) 1998 - 2014, 2017, Daniel Stenberg, <daniel@haxx.se>, et al.
+# Copyright (C) 1998 - 2018, Daniel Stenberg, <daniel@haxx.se>, et al.
 #
 # This software is licensed as described in the file COPYING, which
 # you should have received as part of this distribution. The terms
@@ -920,7 +920,7 @@ sub DATA_smtp {
                 print FILE $line if(!$nosave);
 
                 $raw .= $line;
-                if($raw =~ /\x0d\x0a\x2e\x0d\x0a/) {
+                if($raw =~ /(?:^|\x0d\x0a)\x2e\x0d\x0a/) {
                     # end of data marker!
                     $eob = 1;
                 }