diff --git a/core/regexp/linear_time_spec.rb b/core/regexp/linear_time_spec.rb
index 2f3f81ed2..f70021dfe 100644
--- a/core/regexp/linear_time_spec.rb
+++ b/core/regexp/linear_time_spec.rb
@@ -25,7 +25,56 @@
     }.should complain(/warning: flags ignored/)
   end
 
-  it "returns true for positive lookarounds" do
-    Regexp.linear_time?(/(?:(?=a*)a)*/).should == true
+  it "returns true for positive lookahead" do
+    Regexp.linear_time?(/a*(?:(?=a*)a)*b/).should == true
+  end
+
+  it "returns true for positive lookbehind" do
+    Regexp.linear_time?(/a*(?:(?<=a)a*)*b/).should == true
+  end
+
+  it "returns true for negative lookbehind" do
+    Regexp.linear_time?(/a*(?:(?<!a)a*)*b/).should == true
+  end
+
+  # There are two known ways to make Regexp linear:
+  # * Using a DFA (deterministic finite-state automaton) Regexp engine, which always matches in linear time (e.g. TruffleRuby with TRegex)
+  # * Caching position and state to avoid catastrophic backtracking (e.g. CRuby: https://bugs.ruby-lang.org/issues/19104)
+  #
+  # Both approach should be allowed and given that DFA Regexp engines
+  # are much faster there should be no specs preventing using them.
+  uses_regexp_caching = RUBY_ENGINE == 'ruby'
+  uses_dfa_regexp_engine = !uses_regexp_caching
+
+  # The following specs should not be relied upon,
+  # they are here only to illustrate differences between Regexp engines.
+  guard -> { uses_regexp_caching } do
+    it "returns true for negative lookahead" do
+      Regexp.linear_time?(/a*(?:(?!a*)a*)*b/).should == true
+    end
+
+    it "returns true for atomic groups" do
+      Regexp.linear_time?(/a*(?:(?>a)a*)*b/).should == true
+    end
+
+    it "returns true for possessive quantifiers" do
+      Regexp.linear_time?(/a*(?:(?:a)?+a*)*b/).should == true
+    end
+
+    it "returns true for positive lookbehind with capture group" do
+      Regexp.linear_time?(/.(?<=(a))/).should == true
+    end
+  end
+
+  # The following specs should not be relied upon,
+  # they are here only to illustrate differences between Regexp engines.
+  guard -> { uses_dfa_regexp_engine } do
+    it "returns true for non-recursive subexpression call" do
+      Regexp.linear_time?(/(?<a>a){0}\g<a>/).should == true
+    end
+
+    it "returns true for positive lookahead with capture group" do
+      Regexp.linear_time?(/x+(?=(a))/).should == true
+    end
   end
 end