diff --git a/config/initializers/6_validations.rb b/config/initializers/6_validations.rb
index 3ba9e36c567..83acdc8ab54 100644
--- a/config/initializers/6_validations.rb
+++ b/config/initializers/6_validations.rb
@@ -3,22 +3,23 @@ def storage_name_valid?(name)
 end
 
 def find_parent_path(name, path)
+  parent = Pathname.new(path).realpath.parent
   Gitlab.config.repositories.storages.detect do |n, p|
-    name != n && path.chomp('/').start_with?(p.chomp('/'))
+    name != n && Pathname.new(p).realpath == parent
   end
 end
 
-def error(message)
+def storage_validation_error(message)
   raise "#{message}. Please fix this in your gitlab.yml before starting GitLab."
 end
 
-error('No repository storage path defined') if Gitlab.config.repositories.storages.empty?
+storage_validation_error('No repository storage path defined') if Gitlab.config.repositories.storages.empty?
 
 Gitlab.config.repositories.storages.each do |name, path|
-  error("\"#{name}\" is not a valid storage name") unless storage_name_valid?(name)
+  storage_validation_error("\"#{name}\" is not a valid storage name") unless storage_name_valid?(name)
 
   parent_name, _parent_path = find_parent_path(name, path)
   if parent_name
-    error("#{name} is a nested path of #{parent_name}. Nested paths are not supported for repository storages")
+    storage_validation_error("#{name} is a nested path of #{parent_name}. Nested paths are not supported for repository storages")
   end
 end
diff --git a/spec/initializers/6_validations_spec.rb b/spec/initializers/6_validations_spec.rb
index 5178bd130f4..05d0aa63488 100644
--- a/spec/initializers/6_validations_spec.rb
+++ b/spec/initializers/6_validations_spec.rb
@@ -1,9 +1,19 @@
 require 'spec_helper'
 
 describe '6_validations', lib: true do
+  before :all do
+    FileUtils.mkdir_p('tmp/tests/paths/a/b/c/d')
+    FileUtils.mkdir_p('tmp/tests/paths/a/b/c2')
+    FileUtils.mkdir_p('tmp/tests/paths/a/b/d')
+  end
+
+  after :all do
+    FileUtils.rm_rf('tmp/tests/paths')
+  end
+
   context 'with correct settings' do
     before do
-      mock_storages('foo' => '/a/b/c', 'bar' => 'a/b/d')
+      mock_storages('foo' => 'tmp/tests/paths/a/b/c', 'bar' => 'tmp/tests/paths/a/b/d')
     end
 
     it 'passes through' do
@@ -13,7 +23,7 @@ describe '6_validations', lib: true do
 
   context 'with invalid storage names' do
     before do
-      mock_storages('name with spaces' => '/a/b/c')
+      mock_storages('name with spaces' => 'tmp/tests/paths/a/b/c')
     end
 
     it 'throws an error' do
@@ -23,7 +33,7 @@ describe '6_validations', lib: true do
 
   context 'with nested storage paths' do
     before do
-      mock_storages('foo' => '/a/b/c', 'bar' => '/a/b/c/d')
+      mock_storages('foo' => 'tmp/tests/paths/a/b/c', 'bar' => 'tmp/tests/paths/a/b/c/d')
     end
 
     it 'throws an error' do
@@ -31,6 +41,16 @@ describe '6_validations', lib: true do
     end
   end
 
+  context 'with similar but un-nested storage paths' do
+    before do
+      mock_storages('foo' => 'tmp/tests/paths/a/b/c', 'bar' => 'tmp/tests/paths/a/b/c2')
+    end
+
+    it 'passes through' do
+      expect { load_validations }.not_to raise_error
+    end
+  end
+
   def mock_storages(storages)
     allow(Gitlab.config.repositories).to receive(:storages).and_return(storages)
   end