diff --git a/CHANGELOG.md b/CHANGELOG.md
index dc62b52d..b26951e6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,9 @@ and this project adheres to [Break Versioning](https://www.taoensso.com/break-ve
 
 ## [Unreleased]
 
+### Added
+
+- Improve sum type error handling documentation (addresses #439) (@baweaver)
 
 ## [1.8.3] - 2025-06-09
 
diff --git a/docsite/source/combining-types/sum.html.md b/docsite/source/combining-types/sum.html.md
index 4db36f57..9cfa2a45 100644
--- a/docsite/source/combining-types/sum.html.md
+++ b/docsite/source/combining-types/sum.html.md
@@ -18,3 +18,14 @@ nil_or_string["hello"] # => "hello"
 
 nil_or_string[123] # raises Dry::Types::ConstraintError
 ```
+
+## Error Handling
+
+Sum types try each type from left to right. If all types fail, the error from the rightmost type is raised:
+
+``` ruby
+Value = FixedAmount | Percentage
+
+# Raises error from Percentage (rightmost), not FixedAmount
+Value.call(type: "fixed", value: -1.1)
+```
diff --git a/lib/dry/types/sum.rb b/lib/dry/types/sum.rb
index 7b612ca9..25ff36e9 100644
--- a/lib/dry/types/sum.rb
+++ b/lib/dry/types/sum.rb
@@ -4,6 +4,16 @@ module Dry
   module Types
     # Sum type
     #
+    # Sum types try each constituent type from left to right and return the result
+    # from the first successful type. If all types fail, the error from the rightmost
+    # (last attempted) type is raised, not necessarily the most "relevant" error.
+    #
+    # @example
+    #   # Given: FixedAmount | Percentage
+    #   # Input: { type: "fixed", value: -1.1 }
+    #   # FixedAmount fails on value constraint, Percentage fails on type mismatch
+    #   # Error raised will be from Percentage (rightmost), not FixedAmount
+    #
     # @api public
     class Sum
       include Composition
@@ -19,6 +29,9 @@ def optional? = primitive?(nil)
       #
       # @return [Object]
       #
+      # @note Tries left type first, then right type. If both fail, raises the
+      #   error from the right (last attempted) type for performance reasons.
+      #
       # @api private
       def call_unsafe(input)
         left.call_safe(input) { right.call_unsafe(input) }