diff --git a/guides/getting-started/readme.md b/guides/getting-started/readme.md
index 8568a2c..bcf25de 100644
--- a/guides/getting-started/readme.md
+++ b/guides/getting-started/readme.md
@@ -298,6 +298,14 @@ messy.to_s  # => "https://example.com/a/c/d"
 
 If the original path structure is significant, retain the parsed URL and do not call `normalize!`.
 
+To normalize its encoding and resolve dot segments while preserving repeated separators, compose the path operations explicitly:
+
+``` ruby
+url = Protocol::URL["https://example.com/a//b/./c"]
+url.path = url.path.normalize.simplify(preserve_empty: true)
+url.to_s  # => "https://example.com/a//b/c"
+```
+
 ## Best Practices
 
 ### Choose the Right Class
diff --git a/lib/protocol/url/path.rb b/lib/protocol/url/path.rb
index 4fdc179..758a809 100644
--- a/lib/protocol/url/path.rb
+++ b/lib/protocol/url/path.rb
@@ -291,9 +291,10 @@ def normalize
 			
 			# Simplify this path in place by resolving literal or percent-encoded dot segments and repeated separators.
 			#
+			# @parameter preserve_empty [Boolean] Whether to preserve empty path segments represented by repeated separators.
 			# @returns [Path | Nil] This path when changed, otherwise `nil`.
-			def simplify!
-				simplified = simplify
+			def simplify!(preserve_empty: false)
+				simplified = simplify(preserve_empty: preserve_empty)
 				return nil if simplified.equal?(self)
 				
 				@encoded = simplified.encoded
@@ -307,9 +308,10 @@ def simplify!
 			# Absolute paths do not retain parent components above the root. Relative paths
 			# retain leading parent components which cannot be resolved locally.
 			#
+			# @parameter preserve_empty [Boolean] Whether to preserve empty path segments represented by repeated separators.
 			# @returns [Path] The simplified path, or this path if already canonical.
-			def simplify
-				segments = simplify_segments
+			def simplify(preserve_empty: false)
+				segments = simplify_segments(preserve_empty: preserve_empty)
 				return self unless segments
 				
 				return self.class.new(nil, segments)
@@ -432,7 +434,7 @@ def dot_segment(segment)
 			end
 			
 			# Find the first encoded segment which requires simplification.
-			def simplification_index(segments)
+			def simplification_index(segments, preserve_empty: false)
 				absolute = segments.first == ""
 				regular_segment = false
 				last_index = segments.size - 1
@@ -444,7 +446,9 @@ def simplification_index(segments)
 						return index
 					elsif segment == ""
 						# Leading and trailing empty components are significant.
-						return index if index > 0 && index < last_index
+						if !preserve_empty && index > 0 && index < last_index
+							return index
+						end
 					elsif dot == ".."
 						# Absolute paths cannot retain parent components. Relative paths
 						# can retain them only before the first regular component.
@@ -458,19 +462,19 @@ def simplification_index(segments)
 			end
 			
 			# Return simplified encoded segments, or nil if they are already canonical.
-			def simplify_segments
+			def simplify_segments(preserve_empty: false)
 				segments = self.segments
-				return nil unless start_index = simplification_index(segments)
+				return nil unless start_index = simplification_index(segments, preserve_empty: preserve_empty)
 				
 				segments = segments.dup
-				simplify_segments!(segments, start_index)
+				simplify_segments!(segments, start_index, preserve_empty: preserve_empty)
 				
 				return segments
 			end
 			
 			# Simplify the given encoded segments in place.
-			def simplify_segments!(segments, start_index = nil)
-				start_index ||= simplification_index(segments)
+			def simplify_segments!(segments, start_index = nil, preserve_empty: false)
+				start_index ||= simplification_index(segments, preserve_empty: preserve_empty)
 				return nil unless start_index
 				
 				offset = start_index
@@ -488,10 +492,18 @@ def simplify_segments!(segments, start_index = nil)
 							offset += 1
 						end
 					elsif segment == "" && index != last_index
-						# Collapse repeated separators:
+						# Preserve or collapse repeated separators according to the requested policy:
+						if preserve_empty
+							segments[offset] = segment if offset < index
+							offset += 1
+						end
 					elsif dot == ".." && offset > 0 && dot_segment(segments[offset - 1]) != ".."
 						# Pop a component, but never pop the absolute-path root:
-						offset -= 1 if segments[offset - 1] != ""
+						if preserve_empty
+							offset -= 1 unless segments.first == "" && offset == 1
+						elsif segments[offset - 1] != ""
+							offset -= 1
+						end
 						
 						# A trailing parent reference also denotes a directory.
 						if index == last_index
diff --git a/releases.md b/releases.md
index e051a88..19a14ad 100644
--- a/releases.md
+++ b/releases.md
@@ -3,6 +3,7 @@
 ## Unreleased
 
   - Add conservative normalization of encoded URL paths.
+  - Add an option to preserve empty path segments while simplifying paths.
 
 ## v0.12.0
 
diff --git a/test/protocol/url/path.rb b/test/protocol/url/path.rb
index 4001414..e1274c6 100644
--- a/test/protocol/url/path.rb
+++ b/test/protocol/url/path.rb
@@ -315,6 +315,24 @@
 			
 			expect(path.simplify.encoded).to be == "/b"
 		end
+		
+		it "can preserve repeated separators" do
+			path = Protocol::URL::Path["/a//b///c"]
+			
+			expect(path.simplify(preserve_empty: true)).to be_equal(path)
+		end
+		
+		it "resolves dot segments while preserving repeated separators" do
+			path = Protocol::URL::Path["/a//b/./c/../d"]
+			
+			expect(path.simplify(preserve_empty: true).encoded).to be == "/a//b/d"
+		end
+		
+		it "resolves a parent against an empty segment when preserving repeated separators" do
+			path = Protocol::URL::Path["/a//../b"]
+			
+			expect(path.simplify(preserve_empty: true).encoded).to be == "/a/b"
+		end
 	end
 	
 	with "#normalize" do
@@ -426,6 +444,13 @@
 			path.simplify!
 			expect(path.components).to be == ["", "a", ""]
 		end
+		
+		it "can preserve repeated separators" do
+			path = Protocol::URL::Path["/a//b/./c"]
+			
+			path.simplify!(preserve_empty: true)
+			expect(path.encoded).to be == "/a//b/c"
+		end
 	end
 	
 	with "#join" do