diff --git a/spec/detach_race_condition_spec.rb b/spec/detach_race_condition_spec.rb
index 5d11be2..f1c39a2 100644
--- a/spec/detach_race_condition_spec.rb
+++ b/spec/detach_race_condition_spec.rb
@@ -1,10 +1,13 @@
 require 'spec_helper'
 
 describe Cool.io::Loop do
+  # An IOWatcher that drains its pipe and then runs a user-supplied block,
+  # receiving itself as the argument.
   class Victim < Cool.io::IOWatcher
-    def initialize(io)
-      super
+    def initialize(io, &on_readable)
+      super(io)
       @io = io
+      @on_readable = on_readable
     end
 
     def on_readable
@@ -12,38 +15,57 @@ def on_readable
         @io.read_nonblock(1024)
       rescue IO::WaitReadable, EOFError
       end
+      @on_readable.call(self) if @on_readable
     end
   end
 
   # https://github.com/socketry/cool.io/issues/87
-  it "does not raise TypeError when a watcher is detached while an event is pending" do
-    loop = Cool.io::Loop.default
-
+  #
+  # Several watchers have an event pending in the same loop iteration.  When the
+  # first one dispatched detaches the others, the loop must skip their now-stale
+  # pending events instead of dispatching them to a detached watcher.  Before the
+  # fix that raised "TypeError: wrong argument type nil (expected Coolio::Loop)"
+  # and could crash the VM.
+  #
+  # This is exercised deterministically within a single thread (a preceding
+  # callback detaching another watcher in the same loop cycle).  The original
+  # reproduction detached from a separate thread while the loop was polling,
+  # which is an unsupported concurrent mutation of libev (not thread-safe) and
+  # crashed intermittently on macOS.
+  it "does not raise when a watcher with a pending event is detached during dispatch" do
     iterations = 200
 
     expect {
       iterations.times do
-        r_victim, w_victim = IO.pipe
-        victim_watcher = Victim.new(r_victim)
-        victim_watcher.attach(loop)
-
-        t1 = Thread.new do
-          sleep 0.01
-          w_victim.write("dummy\n")
-        end
-
-        t2 = Thread.new do
-          sleep 0.01
-          victim_watcher.detach
+        coolio_loop = Cool.io::Loop.new
+        pipes = []
+        watchers = []
+
+        5.times do
+          r, w = IO.pipe
+          pipes << [r, w]
+
+          watcher = Victim.new(r) do |fired|
+            # Detach every other watcher whose event is already queued for this
+            # same loop iteration.
+            watchers.each do |other|
+              other.detach if !other.equal?(fired) && other.attached?
+            end
+          end
+          watcher.attach(coolio_loop)
+          watchers << watcher
+
+          w.write("dummy\n") # make the read end readable so an event is pending
         end
 
-        loop.run_once
+        coolio_loop.run_once
 
-        t1.join
-        t2.join
+        # Only the first dispatched watcher runs; it detaches the other four,
+        # whose pending events are then skipped.
+        expect(watchers.count(&:attached?)).to eq(1)
 
-        r_victim.close
-        w_victim.close
+        watchers.each { |watcher| watcher.detach if watcher.attached? }
+        pipes.each { |r, w| r.close; w.close }
       end
     }.not_to raise_error
   end