diff --git a/lib/rubygems/specification_policy.rb b/lib/rubygems/specification_policy.rb
index a05edcd5c9c6..ae9517b579c4 100644
--- a/lib/rubygems/specification_policy.rb
+++ b/lib/rubygems/specification_policy.rb
@@ -125,15 +125,17 @@ def validate_dependencies # :nodoc:
 
       seen[dep.type][dep.name] = dep
 
-      prerelease_dep = dep.requirements_list.any? do |req|
-        Gem::Requirement.new(req).prerelease?
+      dep_requirements = dep.requirement.requirements
+
+      prerelease_dep = dep_requirements.any? do |op, version|
+        version.prerelease? and op != '<'
       end
 
       warning_messages << "prerelease dependency on #{dep} is not recommended" if
           prerelease_dep && !version.prerelease?
 
-      overly_strict = dep.requirement.requirements.length == 1 &&
-          dep.requirement.requirements.any? do |op, version|
+      overly_strict = dep_requirements.length == 1 &&
+          dep_requirements.any? do |op, version|
             op == '~>' and
                 not version.prerelease? and
                 version.segments.length > 2 and
@@ -141,7 +143,7 @@ def validate_dependencies # :nodoc:
           end
 
       if overly_strict then
-        _, dep_version = dep.requirement.requirements.first
+        _, dep_version = dep_requirements.first
 
         base = dep_version.segments.first 2
         upper_bound = dep_version.segments.first(dep_version.segments.length - 1)
@@ -156,12 +158,12 @@ def validate_dependencies # :nodoc:
         WARNING
       end
 
-      open_ended = dep.requirement.requirements.all? do |op, version|
+      open_ended = dep_requirements.all? do |op, version|
         not version.prerelease? and (op == '>' or op == '>=')
       end
 
       if open_ended then
-        op, dep_version = dep.requirement.requirements.first
+        op, dep_version = dep_requirements.first
 
         base = dep_version.segments.first 2
 
diff --git a/test/rubygems/test_gem_specification.rb b/test/rubygems/test_gem_specification.rb
index 34665edec1f1..8aee50e43b66 100644
--- a/test/rubygems/test_gem_specification.rb
+++ b/test/rubygems/test_gem_specification.rb
@@ -2650,6 +2650,7 @@ def test_validate_dependencies
       @a1.add_runtime_dependency     'l', '> 1.2.3'
       @a1.add_runtime_dependency     'm', '~> 2.1.0'
       @a1.add_runtime_dependency     'n', '~> 0.1.0'
+      @a1.add_runtime_dependency     'o', '< 1.0.x'
 
       use_ui @ui do
         @a1.validate