diff --git a/lib/utopia/path.rb b/lib/utopia/path.rb
index b6422cf..af3a1de 100644
--- a/lib/utopia/path.rb
+++ b/lib/utopia/path.rb
@@ -215,19 +215,34 @@ def -(other)
 		end
 		
 		def simplify
-			result = absolute? ? [""] : []
+			components = []
 			
-			@components.each do |bit|
-				if bit == ".."
-					result.pop
-				elsif bit != "." && bit != ""
-					result << bit
-				end
+			index = 0
+			
+			if @components[0] == ""
+				components << ""
+				index += 1
 			end
 			
-			result << "" if directory?
+			while index < @components.size
+				bit = @components[index]
+				if bit == "."
+					# No-op (ignore current directory)
+				elsif bit == "" && index != @components.size - 1
+					# No-op (ignore multiple slashes)
+				elsif bit == ".." && components.last && components.last != ".."
+					if components.last != ""
+						# We can go up one level:
+						components.pop
+					end
+				else
+					components << bit
+				end
+				
+				index += 1
+			end
 			
-			return self.class.new(result)
+			return self.class.new(components)
 		end
 		
 		# Returns the first path component.
diff --git a/releases.md b/releases.md
index 94236dd..47890ec 100644
--- a/releases.md
+++ b/releases.md
@@ -3,6 +3,7 @@
 ## Unreleased
 
   - Add agent context.
+  - Better simplification of relative paths, e.g. `../../foo` is not modified to `foo`.
 
 ## v2.30.1
 
diff --git a/test/utopia/path.rb b/test/utopia/path.rb
index d7bdbfd..417f2b8 100755
--- a/test/utopia/path.rb
+++ b/test/utopia/path.rb
@@ -195,6 +195,7 @@
 			expect(directory.to_directory).to be == directory
 		end
 	end
+	
 	it "should start with the given path" do
 		path = Utopia::Path["/a/b/c/d/e"]
 		
@@ -263,4 +264,59 @@
 		
 		expect((output + short).simplify).to be == input
 	end
+	
+	with "#simplify" do
+		it "doesn't remove leading .. from relative paths" do
+			path = Utopia::Path["../foo/bar"]
+			simplified = path.simplify
+			
+			expect(simplified.components).to be == ["..", "foo", "bar"]
+		end
+		
+		it "removes redundant .. from absolute paths" do
+			path = Utopia::Path["/foo/../../bar"]
+			simplified = path.simplify
+			
+			expect(simplified.components).to be == ["", "bar"]
+		end
+		
+		it "preserves excess .. for purely relative paths" do
+			# ../../foo cannot be reduced without a base; keep leading .. components
+			path = Utopia::Path["../../foo"]
+			simplified = path.simplify
+			
+			expect(simplified.components).to be == ["..", "..", "foo"]
+		end
+		
+		it "reduces relative paths only as far as components allow" do
+			# foo/../../bar -> ../bar (pop foo for first .., then keep remaining ..)
+			path = Utopia::Path["foo/../../bar"]
+			simplified = path.simplify
+			
+			expect(simplified.components).to be == ["..", "bar"]
+		end
+		
+		it "does not traverse above root for absolute paths" do
+			# /a/b/../../../c -> /c (ignore .. beyond root)
+			path = Utopia::Path["/a/b/../../../c"]
+			simplified = path.simplify
+			
+			expect(simplified.components).to be == ["", "c"]
+		end
+		
+		it "ignores leading .. at absolute root" do
+			# /../../c -> /c
+			path = Utopia::Path["/../../c"]
+			simplified = path.simplify
+			
+			expect(simplified.components).to be == ["", "c"]
+		end
+		
+		it "preserves trailing slash for directories after simplify" do
+			path = Utopia::Path["/a/./b/../c/"]
+			simplified = path.simplify
+			
+			expect(simplified.components).to be == ["", "a", "c", ""]
+		end
+	end
 end