diff --git a/spec/bundler/bundler/endpoint_specification_spec.rb b/spec/bundler/bundler/endpoint_specification_spec.rb
index e7e10730cfde10..6518f125ba5e52 100644
--- a/spec/bundler/bundler/endpoint_specification_spec.rb
+++ b/spec/bundler/bundler/endpoint_specification_spec.rb
@@ -42,7 +42,7 @@
         expect { subject }.to raise_error(
           Bundler::GemspecError,
           a_string_including("There was an error parsing the metadata for the gem foo (1.0.0)").
-            and(a_string_including('The metadata was {"rubygems"=>">\n"}'))
+            and(a_string_including("The metadata was #{{ "rubygems" => ">\n" }.inspect}"))
         )
       end
     end
diff --git a/spec/bundler/install/gems/compact_index_spec.rb b/spec/bundler/install/gems/compact_index_spec.rb
index 39064e3b80b219..4653ce6d871726 100644
--- a/spec/bundler/install/gems/compact_index_spec.rb
+++ b/spec/bundler/install/gems/compact_index_spec.rb
@@ -173,7 +173,7 @@
     bundle :install, verbose: true, artifice: "compact_index_checksum_mismatch"
     expect(out).to include("Fetching gem metadata from #{source_uri}")
     expect(out).to include("The checksum of /versions does not match the checksum provided by the server!")
-    expect(out).to include('Calculated checksums {"sha-256"=>"8KfZiM/fszVkqhP/m5s9lvE6M9xKu4I1bU4Izddp5Ms="} did not match expected {"sha-256"=>"ungWv48Bz+pBQUDeXa4iI7ADYaOWF3qctBD/YfIAFa0="}')
+    expect(out).to include("Calculated checksums #{{ "sha-256" => "8KfZiM/fszVkqhP/m5s9lvE6M9xKu4I1bU4Izddp5Ms=" }.inspect} did not match expected #{{ "sha-256" => "ungWv48Bz+pBQUDeXa4iI7ADYaOWF3qctBD/YfIAFa0=" }.inspect}")
     expect(the_bundle).to include_gems "myrack 1.0.0"
   end
 
diff --git a/test/error_highlight/test_error_highlight.rb b/test/error_highlight/test_error_highlight.rb
index 5f4c386990c76d..0a21f3b283fa2b 100644
--- a/test/error_highlight/test_error_highlight.rb
+++ b/test/error_highlight/test_error_highlight.rb
@@ -1232,7 +1232,7 @@ def custom_formatter.message_for(spot)
     assert_error_message(NoMethodError, <<~END) do
 undefined method `time' for #{ ONE_RECV_MESSAGE }
 
-{:first_lineno=>#{ __LINE__ + 3 }, :first_column=>7, :last_lineno=>#{ __LINE__ + 3 }, :last_column=>12, :snippet=>"      1.time {}\\n"}
+#{{ first_lineno: __LINE__ + 3, first_column: 7, last_lineno: __LINE__ + 3, last_column: 12, snippet: "      1.time {}\n" }.inspect}
     END
 
       1.time {}
diff --git a/test/rdoc/test_rdoc_ri_driver.rb b/test/rdoc/test_rdoc_ri_driver.rb
index 39e6e677596dbd..3263e6173ef001 100644
--- a/test/rdoc/test_rdoc_ri_driver.rb
+++ b/test/rdoc/test_rdoc_ri_driver.rb
@@ -54,10 +54,10 @@ def test_self_dump
       RDoc::RI::Driver.dump @store1.cache_path
     end
 
-    assert_match %r%:class_methods%,    out
-    assert_match %r%:modules%,          out
-    assert_match %r%:instance_methods%, out
-    assert_match %r%:ancestors%,        out
+    assert_match %r%:class_methods|class_methods:%,       out
+    assert_match %r%:modules|modules:%,                   out
+    assert_match %r%:instance_methods|instance_methods:%, out
+    assert_match %r%:ancestors|ancestors:%,               out
   end
 
   def test_add_also_in_empty
diff --git a/test/rubygems/test_gem_dependency.rb b/test/rubygems/test_gem_dependency.rb
index 2a989a55513b99..a0bfee023936cb 100644
--- a/test/rubygems/test_gem_dependency.rb
+++ b/test/rubygems/test_gem_dependency.rb
@@ -22,7 +22,7 @@ def test_initialize_type_bad
       Gem::Dependency.new "monkey" => "1.0"
     end
 
-    assert_equal 'dependency name must be a String, was {"monkey"=>"1.0"}',
+    assert_equal "dependency name must be a String, was #{{ "monkey" => "1.0" }.inspect}",
                  e.message
   end
 
diff --git a/test/rubygems/test_require.rb b/test/rubygems/test_require.rb
index 42a31452ae5516..206051c27051eb 100644
--- a/test/rubygems/test_require.rb
+++ b/test/rubygems/test_require.rb
@@ -705,11 +705,11 @@ def test_require_bundler
         _, err = capture_subprocess_io do
           system(*ruby_with_rubygems_in_load_path, "-w", "--disable=gems", "-C", dir, "main.rb")
         end
-        assert_match(/{:x=>1}\n{:y=>2}\n$/, err)
+        assert_match(/#{{ x: 1 }.inspect}\n#{{ y: 2 }.inspect}\n$/, err)
         _, err = capture_subprocess_io do
           system(*ruby_with_rubygems_in_load_path, "-w", "--enable=gems", "-C", dir, "main.rb")
         end
-        assert_match(/{:x=>1}\n{:y=>2}\n$/, err)
+        assert_match(/#{{ x: 1 }.inspect}\n#{{ y: 2 }.inspect}\n$/, err)
       end
     end
   end