diff --git a/lib/bundler/vendor/connection_pool/lib/connection_pool.rb b/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
index 317088a866..cb4485e463 100644
--- a/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
+++ b/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
@@ -160,6 +160,12 @@ class Bundler::ConnectionPool
     @available.shutdown(reload: true, &block)
   end
 
+  ## Reaps idle connections that have been idle for over +idle_seconds+.
+  # +idle_seconds+ defaults to 60.
+  def reap(idle_seconds = 60, &block)
+    @available.reap(idle_seconds, &block)
+  end
+
   # Size of this connection pool
   attr_reader :size
   # Automatically drop all connections after fork
@@ -169,6 +175,11 @@ class Bundler::ConnectionPool
   def available
     @available.length
   end
+
+  # Number of pool entries created and idle in the pool.
+  def idle
+    @available.idle
+  end
 end
 
 require_relative "connection_pool/timed_stack"
diff --git a/lib/bundler/vendor/connection_pool/lib/connection_pool/timed_stack.rb b/lib/bundler/vendor/connection_pool/lib/connection_pool/timed_stack.rb
index 35d1d7cc35..02e4485eb2 100644
--- a/lib/bundler/vendor/connection_pool/lib/connection_pool/timed_stack.rb
+++ b/lib/bundler/vendor/connection_pool/lib/connection_pool/timed_stack.rb
@@ -41,6 +41,7 @@ class Bundler::ConnectionPool::TimedStack
   def push(obj, options = {})
     @mutex.synchronize do
       if @shutdown_block
+        @created -= 1 unless @created == 0
         @shutdown_block.call(obj)
       else
         store_connection obj, options
@@ -98,6 +99,26 @@ class Bundler::ConnectionPool::TimedStack
     end
   end
 
+  ##
+  # Reaps connections that were checked in more than +idle_seconds+ ago.
+  def reap(idle_seconds, &block)
+    raise ArgumentError, "reap must receive a block" unless block
+    raise ArgumentError, "idle_seconds must be a number" unless idle_seconds.is_a?(Numeric)
+    raise Bundler::ConnectionPool::PoolShuttingDownError if @shutdown_block
+
+    idle.times do
+      conn =
+        @mutex.synchronize do
+          raise Bundler::ConnectionPool::PoolShuttingDownError if @shutdown_block
+
+          reserve_idle_connection(idle_seconds)
+        end
+      break unless conn
+
+      block.call(conn)
+    end
+  end
+
   ##
   # Returns +true+ if there are no available connections.
 
@@ -112,6 +133,12 @@ class Bundler::ConnectionPool::TimedStack
     @max - @created + @que.length
   end
 
+  ##
+  # The number of connections created and available on the stack.
+  def idle
+    @que.length
+  end
+
   private
 
   def current_time
@@ -133,7 +160,7 @@ class Bundler::ConnectionPool::TimedStack
   # This method must return a connection from the stack.
 
   def fetch_connection(options = nil)
-    @que.pop
+    @que.pop&.first
   end
 
   ##
@@ -144,9 +171,32 @@ class Bundler::ConnectionPool::TimedStack
   def shutdown_connections(options = nil)
     while connection_stored?(options)
       conn = fetch_connection(options)
+      @created -= 1 unless @created == 0
       @shutdown_block.call(conn)
     end
-    @created = 0
+  end
+
+  ##
+  # This is an extension point for TimedStack and is called with a mutex.
+  #
+  # This method returns the oldest idle connection if it has been idle for more than idle_seconds.
+  # This requires that the stack is kept in order of checked in time (oldest first).
+
+  def reserve_idle_connection(idle_seconds)
+    return unless idle_connections?(idle_seconds)
+
+    @created -= 1 unless @created == 0
+
+    @que.shift.first
+  end
+
+  ##
+  # This is an extension point for TimedStack and is called with a mutex.
+  #
+  # Returns true if the first connection in the stack has been idle for more than idle_seconds
+
+  def idle_connections?(idle_seconds)
+    connection_stored? && (current_time - @que.first.last > idle_seconds)
   end
 
   ##
@@ -155,7 +205,7 @@ class Bundler::ConnectionPool::TimedStack
   # This method must return +obj+ to the stack.
 
   def store_connection(obj, options = nil)
-    @que.push obj
+    @que.push [obj, current_time]
   end
 
   ##
diff --git a/lib/bundler/vendor/connection_pool/lib/connection_pool/version.rb b/lib/bundler/vendor/connection_pool/lib/connection_pool/version.rb
index 384d6fc977..88a3714fb8 100644
--- a/lib/bundler/vendor/connection_pool/lib/connection_pool/version.rb
+++ b/lib/bundler/vendor/connection_pool/lib/connection_pool/version.rb
@@ -1,3 +1,3 @@
 class Bundler::ConnectionPool
-  VERSION = "2.4.1"
+  VERSION = "2.5.0"
 end