diff --git a/activesupport/lib/active_support/deprecation.rb b/activesupport/lib/active_support/deprecation.rb
index 22a50f7e8b5df740f73d33f6e587abd62a248905..e4e1d187a5c8f690d2fef553ee9127bebb6a42a5 100644
--- a/activesupport/lib/active_support/deprecation.rb
+++ b/activesupport/lib/active_support/deprecation.rb
@@ -86,11 +86,11 @@ def #{target}_with_deprecation#{punctuation}(*args, &block)
 
     module Assertions
       def assert_deprecated(match = nil, &block)
-        last = collect_deprecations(&block).last
-        assert last, "Expected a deprecation warning within the block but received none"
+        warnings = collect_deprecations(&block)
+        assert !warnings.empty?, "Expected a deprecation warning within the block but received none"
         if match
           match = Regexp.new(Regexp.escape(match)) unless match.is_a?(Regexp)
-          assert_match match, last, "Deprecation warning didn't match #{match}: #{last}"
+          assert warnings.any? { |w| w =~ match }, "No deprecation warning matched #{match}: #{warnings.join(', ')}"
         end
       end
 
diff --git a/activesupport/test/deprecation_test.rb b/activesupport/test/deprecation_test.rb
index 12fe5f3bf20d2b4d991b6e84b1e71c0226ff0506..a7d833f49d23e4ad68a410d0a66d1d50dbde5937 100644
--- a/activesupport/test/deprecation_test.rb
+++ b/activesupport/test/deprecation_test.rb
@@ -78,6 +78,15 @@ def test_assert_deprecation_without_match
     end
   end
 
+  def test_assert_deprecated_matches_any_warning
+    assert_deprecated 'abc' do
+      ActiveSupport::Deprecation.warn 'abc'
+      ActiveSupport::Deprecation.warn 'def'
+    end
+  rescue Test::Unit::AssertionFailedError
+    flunk 'assert_deprecated should match any warning in block, not just the last one'
+  end
+
   def test_silence
     ActiveSupport::Deprecation.silence do
       assert_not_deprecated { @dtc.partially }