diff --git a/lib/power_assert.rb b/lib/power_assert.rb
index 8de209e..5475c71 100644
--- a/lib/power_assert.rb
+++ b/lib/power_assert.rb
@@ -37,13 +37,15 @@ def app_caller_locations
     end
 
     def app_context?
-      top_frame = caller_locations.drop_while {|i| i.path.start_with?(POWER_ASSERT_LIB_DIR) }.first
+      top_frame = caller_locations.drop_while {|i| i.path&.start_with?(POWER_ASSERT_LIB_DIR) }.first
       top_frame and ! internal_file?(top_frame.path)
     end
 
     private
 
     def internal_file?(file)
+      return false unless file
+
       INTERNAL_LIB_DIRS.find do |_, dir|
         file.start_with?(dir)
       end
diff --git a/test/nil_path_location_test.rb b/test/nil_path_location_test.rb
new file mode 100644
index 0000000..8b1a312
--- /dev/null
+++ b/test/nil_path_location_test.rb
@@ -0,0 +1,32 @@
+require_relative 'test_helper'
+
+class TestNilPathLocation < Test::Unit::TestCase
+  include PowerAssertTestHelper
+
+  t do
+    obj = []
+    def obj.foo; self; end
+    enum = Enumerator.new {|y| y << obj.foo }
+    def enum.inspect; '#<Enumerator>'; end
+    assert_equal <<END.chomp, assertion_message {
+      enum.next.foo
+      |    |    |
+      |    |    []
+      |    []
+      #<Enumerator>
+END
+      enum.next.foo
+    }
+  end
+
+  t do
+    # Yielding on a non-target thread keeps the `TracePoint` for `:call` and `:c_call` events enabled while
+    # the `Enumerator`'s fiber runs, so that `app_context?` walks caller locations containing a frame without a path.
+    enum = Enumerator.new {|y| y << 1 }
+    message = ::PowerAssert.start(-> { enum.next }) do |pa|
+      Thread.new { pa.yield }.join
+      pa.message
+    end
+    assert_equal '', message
+  end
+end