diff --git a/CHANGELOG.md b/CHANGELOG.md
index 954aa1ae..9c9a4ca6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -20,6 +20,11 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   JVM could garbage-collect llhttp's native callback trampolines while a parser
   was still in use, after which `llhttp_execute` succeeded without invoking any
   callbacks. Callback procs are now retained for the lifetime of the parser.
+- An IO request body is now rewound when writing it fails partway, not only
+  after it is sent in full. Previously a retried request (e.g. via
+  `.retriable` after a connection reset mid-upload) sent the body from where
+  the failed write stopped: fewer bytes than its `Content-Length`, so the
+  server waited for the rest until the read timed out.
 
 ## [6.0.4] - 2026-07-14
 
diff --git a/lib/http/request/body.rb b/lib/http/request/body.rb
index 9d260ee0..a99897d2 100644
--- a/lib/http/request/body.rb
+++ b/lib/http/request/body.rb
@@ -90,8 +90,7 @@ def each(&block)
         if @source.is_a?(String)
           yield @source
         elsif @source.respond_to?(:read)
-          IO.copy_stream(@source, ProcIO.new(block))
-          rewind(@source)
+          copy_io(block)
         elsif @source
           @source.each(&block)
         end
@@ -112,6 +111,20 @@ def ==(other)
 
       private
 
+      # Stream an IO source to the block, then rewind it
+      #
+      # The rewind also runs when the block raises, so a retried request
+      # sends the whole body again instead of the unsent remainder.
+      #
+      # @param [Proc] block
+      # @return [void]
+      # @api private
+      def copy_io(block)
+        IO.copy_stream(@source, ProcIO.new(block))
+      ensure
+        rewind(@source)
+      end
+
       # Rewind an IO source if possible
       # @return [void]
       # @api private
diff --git a/sig/http.rbs b/sig/http.rbs
index 9b1c4a69..3e9af31d 100644
--- a/sig/http.rbs
+++ b/sig/http.rbs
@@ -906,6 +906,7 @@ module HTTP
 
       private
 
+      def copy_io: ((^(String) -> void)? block) -> void
       def rewind: (untyped io) -> void
       def validate_source_type!: () -> void
 
diff --git a/test/http/request/body_test.rb b/test/http/request/body_test.rb
index 8bacbca8..f22aa9db 100644
--- a/test/http/request/body_test.rb
+++ b/test/http/request/body_test.rb
@@ -156,6 +156,24 @@ def test_each_when_body_is_an_enumerable_io_allows_multiple_enumerations
     assert(results.all?(data))
   end
 
+  def test_each_when_body_is_an_io_rewinds_it_when_a_chunk_fails_to_write
+    data = ("a" * 16 * 1024) + ("b" * 10 * 1024)
+    subject = build_body(StringIO.new(data))
+    written = 0
+
+    assert_raises(Errno::EPIPE) do
+      subject.each do |chunk|
+        raise Errno::EPIPE if written.positive?
+
+        written += chunk.bytesize
+      end
+    end
+
+    chunks = subject.enum_for(:each).map(&:dup)
+
+    assert_equal data, chunks.sum("")
+  end
+
   def test_each_when_body_is_an_enumerable_yields_elements
     chunks = build_body(%w[bees cows]).enum_for(:each).map(&:dup)