diff --git a/lib/bundler/shared_helpers.rb b/lib/bundler/shared_helpers.rb
index 45185209f14..3d488326d68 100644
--- a/lib/bundler/shared_helpers.rb
+++ b/lib/bundler/shared_helpers.rb
@@ -336,7 +336,12 @@ def clean_load_path
       loaded_gem_paths = Bundler.rubygems.loaded_gem_paths
 
       $LOAD_PATH.reject! do |p|
-        next if File.expand_path(p).start_with?(bundler_lib)
+        expanded_p = File.expand_path(p)
+        if File.exist?(expanded_p) && File.respond_to?(:realpath)
+          path = File.realpath(expanded_p)
+          next if path.start_with?(bundler_lib)
+        end
+        next if expanded_p.start_with?(bundler_lib)
         loaded_gem_paths.delete(p)
       end
       $LOAD_PATH.uniq!
diff --git a/spec/runtime/setup_spec.rb b/spec/runtime/setup_spec.rb
index e84cdaabf5c..2d2aff78a71 100644
--- a/spec/runtime/setup_spec.rb
+++ b/spec/runtime/setup_spec.rb
@@ -857,6 +857,47 @@ def clean_load_path(lp)
     expect(out).to eq("true\ntrue")
   end
 
+  context "with bundler is located in symlinked GEM_HOME" do
+    let(:gem_home) { Dir.mktmpdir }
+    let(:symlinked_gem_home) { Tempfile.new }
+    let(:bundler_dir) { File.expand_path("../..", __dir__) }
+    let(:bundler_lib) { File.join(bundler_dir, lib) }
+    before do
+      FileUtils.ln_sf(gem_home, symlinked_gem_home)
+      gems_dir = File.join(gem_home, "gems")
+      specifications_dir = File.join(gem_home, "specifications")
+      Dir.mkdir(gems_dir)
+      Dir.mkdir(specifications_dir)
+
+      FileUtils.ln_s(bundler_dir, File.join(gems_dir, "bundler-#{Bundler::VERSION}"))
+
+      gemspec = File.read("#{bundler_dir}/bundler.gemspec").
+                sub("Bundler::VERSION", %("#{Bundler::VERSION}"))
+      gemspec = gemspec.lines.grep_v(%r{lib/bundler/version}).join
+
+      File.open(File.join(specifications_dir, "bundler.gemspec"), "wb") do |f|
+        f.write(gemspec)
+      end
+    end
+
+    it "should succesfully require 'bundler/setup'" do
+      install_gemfile ""
+
+      ENV["GEM_PATH"] = symlinked_gem_home.to_path
+
+      ruby <<-R
+        if $LOAD_PATH,include?(bundler_lib)
+          $LOAD_PATH.delete(bundler_lib)
+        else
+          raise "We don't have #{bundler_lib} in $LOAD_PATH"
+        end
+        puts (require 'bundler/setup')
+      R
+
+      expect(out).to eql("true")
+    end
+  end
+
   it "stubs out Gem.refresh so it does not reveal system gems" do
     system_gems "rack-1.0.0"