diff --git a/jekyll.gemspec b/jekyll.gemspec
index 7ce48c614e1..fc8a5937604 100644
--- a/jekyll.gemspec
+++ b/jekyll.gemspec
@@ -30,7 +30,7 @@ Gem::Specification.new do |s|
 
   s.add_runtime_dependency('liquid', "~> 2.5.5")
   s.add_runtime_dependency('classifier', "~> 1.3")
-  s.add_runtime_dependency('listen', "~> 2.5")
+  s.add_runtime_dependency('listen', [">= 2.7.6", "< 3.0.0"])
   s.add_runtime_dependency('kramdown', "~> 1.3")
   s.add_runtime_dependency('pygments.rb', "~> 0.5.0")
   s.add_runtime_dependency('mercenary', "~> 0.3.3")