diff --git a/app/assets/javascripts/discourse/dialects/dialect.js b/app/assets/javascripts/discourse/dialects/dialect.js
index 302597b66f2..58bb55f7a17 100644
--- a/app/assets/javascripts/discourse/dialects/dialect.js
+++ b/app/assets/javascripts/discourse/dialects/dialect.js
@@ -64,7 +64,7 @@ function invalidBoundary(args, prev) {
   var last = prev[prev.length - 1];
   if (typeof last !== "string") { return; }
 
-  if (args.wordBoundary && (!last.match(/\W$/))) { return true; }
+  if (args.wordBoundary && (last.match(/(\w|\/)$/))) { return true; }
   if (args.spaceBoundary && (!last.match(/\s$/))) { return true; }
 }
 
diff --git a/test/javascripts/components/markdown_test.js b/test/javascripts/components/markdown_test.js
index ef2d5e9dbfe..9f53d070582 100644
--- a/test/javascripts/components/markdown_test.js
+++ b/test/javascripts/components/markdown_test.js
@@ -23,6 +23,7 @@ test("basic cooking", function() {
   cooked("_trout_", "<p><em>trout</em></p>", "it italicizes text.");
   cooked("***hello***", "<p><strong><em>hello</em></strong></p>", "it can do bold and italics at once.");
   cooked("word_with_underscores", "<p>word_with_underscores</p>", "it doesn't do intraword italics");
+  cooked("common/_special_font_face.html.erb", "<p>common/_special_font_face.html.erb</p>", "it doesn't intraword with a slash");
   cooked("hello \\*evil\\*", "<p>hello *evil*</p>", "it supports escaping of asterisks");
   cooked("hello \\_evil\\_", "<p>hello _evil_</p>", "it supports escaping of italics");
   cooked("brussel sproutes are *awful*.", "<p>brussel sproutes are <em>awful</em>.</p>", "it doesn't swallow periods.");