diff --git a/src/google/protobuf/io/tokenizer.cc b/src/google/protobuf/io/tokenizer.cc
index 992d8c0b173b..4d7f56cc55f9 100644
--- a/src/google/protobuf/io/tokenizer.cc
+++ b/src/google/protobuf/io/tokenizer.cc
@@ -746,6 +746,8 @@ class CommentCollector {
       : prev_trailing_comments_(prev_trailing_comments),
         detached_comments_(detached_comments),
         next_leading_comments_(next_leading_comments),
+        num_comments_(0),
+        has_trailing_comment_(false),
         has_comment_(false),
         is_line_comment_(false),
         can_attach_to_prev_(true) {
@@ -797,6 +799,7 @@ class CommentCollector {
         if (prev_trailing_comments_ != NULL) {
           prev_trailing_comments_->append(comment_buffer_);
         }
+        has_trailing_comment_ = true;
         can_attach_to_prev_ = false;
       } else {
         if (detached_comments_ != NULL) {
@@ -804,17 +807,39 @@ class CommentCollector {
         }
       }
       ClearBuffer();
+      num_comments_++;
     }
   }
 
   void DetachFromPrev() { can_attach_to_prev_ = false; }
 
+  void MaybeDetachComment() {
+    int count = num_comments_;
+    if (has_comment_) count++;
+
+    // If there's one comment, make sure it is detached.
+    if (count == 1) {
+      if (has_trailing_comment_ && prev_trailing_comments_ != NULL) {
+        std::string trail = *prev_trailing_comments_;
+        if (detached_comments_ != NULL) {
+          // push trailing comment to front of detached
+          detached_comments_->insert(detached_comments_->begin(), 1, trail);
+        }
+        prev_trailing_comments_->clear();
+      }
+      // flush pending comment so it's detached instead of leading
+      Flush();
+    }
+  }
+
  private:
   std::string* prev_trailing_comments_;
   std::vector<std::string>* detached_comments_;
   std::string* next_leading_comments_;
 
   std::string comment_buffer_;
+  int num_comments_;
+  bool has_trailing_comment_;
 
   // True if any comments were read into comment_buffer_.  This can be true even
   // if comment_buffer_ is empty, namely if the comment was "/**/".
@@ -836,6 +861,9 @@ bool Tokenizer::NextWithComments(std::string* prev_trailing_comments,
   CommentCollector collector(prev_trailing_comments, detached_comments,
                              next_leading_comments);
 
+  int prev_line = line_;
+  int trailing_comment_end_line = -1;
+
   if (current_.type == TYPE_START) {
     // Ignore unicode byte order mark(BOM) if it appears at the file
     // beginning. Only UTF-8 BOM (0xEF 0xBB 0xBF) is accepted.
@@ -849,12 +877,14 @@ bool Tokenizer::NextWithComments(std::string* prev_trailing_comments,
       }
     }
     collector.DetachFromPrev();
+    prev_line = -1;
   } else {
     // A comment appearing on the same line must be attached to the previous
     // declaration.
     ConsumeZeroOrMore<WhitespaceNoNewline>();
     switch (TryConsumeCommentStart()) {
       case LINE_COMMENT:
+        trailing_comment_end_line = line_;
         ConsumeLineComment(collector.GetBufferForLineComment());
 
         // Don't allow comments on subsequent lines to be attached to a trailing
@@ -863,14 +893,8 @@ bool Tokenizer::NextWithComments(std::string* prev_trailing_comments,
         break;
       case BLOCK_COMMENT:
         ConsumeBlockComment(collector.GetBufferForBlockComment());
-
+        trailing_comment_end_line = line_;
         ConsumeZeroOrMore<WhitespaceNoNewline>();
-        if (!TryConsume('\n')) {
-          // Oops, the next token is on the same line.  If we recorded a comment
-          // we really have no idea which token it should be attached to.
-          collector.ClearBuffer();
-          return Next();
-        }
 
         // Don't allow comments on subsequent lines to be attached to a trailing
         // comment.
@@ -918,6 +942,13 @@ bool Tokenizer::NextWithComments(std::string* prev_trailing_comments,
             // makes no sense to attach a comment to the following token.
             collector.Flush();
           }
+          if (prev_line == line_ || trailing_comment_end_line == line_) {
+            // When previous token and this one are on the same line, or
+            // even if a multi-line trailing comment ends on the same line
+            // as this token, it's unclear to what token the comment
+            // should be attached. So we detach it.
+            collector.MaybeDetachComment();
+          }
           return result;
         }
         break;
diff --git a/src/google/protobuf/io/tokenizer_unittest.cc b/src/google/protobuf/io/tokenizer_unittest.cc
index 40a24c8e9d46..f4d70f0d51d8 100644
--- a/src/google/protobuf/io/tokenizer_unittest.cc
+++ b/src/google/protobuf/io/tokenizer_unittest.cc
@@ -651,10 +651,10 @@ DocCommentCase kDocCommentCases[] = {
      {},
      ""},
 
-    {"prev /* ignored */ next",
+    {"prev /* detached */ next",
 
      "",
-     {},
+     {" detached "},
      ""},
 
     {"prev // trailing comment\n"
@@ -664,6 +664,13 @@ DocCommentCase kDocCommentCases[] = {
      {},
      ""},
 
+    {"prev\n"
+     "/* leading comment */ next",
+
+     "",
+     {},
+     " leading comment "},
+
     {"prev\n"
      "// leading comment\n"
      "// line 2\n"
@@ -763,6 +770,45 @@ DocCommentCase kDocCommentCases[] = {
      "",
      {},
      " leading comment\n"},
+
+    {"prev /* many comments*/ /* all inline */ /* will be handled */ next",
+
+     " many comments",
+     {" all inline "},
+     " will be handled "},
+
+    {R"pb(
+     prev /* a single block comment
+         that spans multiple lines
+         is detached if it ends
+         on the same line as next */ next"
+     )pb",
+
+     "",
+     {" a single block comment\n"
+      "that spans multiple lines\n"
+      "is detached if it ends\n"
+      "on the same line as next "},
+     ""},
+
+    {R"pb(
+     prev /* trailing */ /* leading */ next"
+     )pb",
+
+     " trailing ",
+     {},
+     " leading "},
+
+    {R"pb(
+     prev /* multi-line
+          trailing */ /* an oddly
+                      placed detached */ /* an oddly
+                                         placed leading */ next"
+     )pb",
+
+     " multi-line\ntrailing ",
+     {" an oddly\nplaced detached "},
+     " an oddly\nplaced leading "},
 };
 
 TEST_2D(TokenizerTest, DocComments, kDocCommentCases, kBlockSizes) {