diff --git a/gems/aws-sdk-core/CHANGELOG.md b/gems/aws-sdk-core/CHANGELOG.md
index 05e3131d8f3..4b2d0f04e4a 100644
--- a/gems/aws-sdk-core/CHANGELOG.md
+++ b/gems/aws-sdk-core/CHANGELOG.md
@@ -1,6 +1,8 @@
 Unreleased Changes
 ------------------
 
+* Issue - Don't retry streaming requests with blocks (#2311)
+
 3.99.1 (2020-06-11)
 ------------------
 
diff --git a/gems/aws-sdk-core/lib/seahorse/client/block_io.rb b/gems/aws-sdk-core/lib/seahorse/client/block_io.rb
index 75af80c8689..9430ae6e99a 100644
--- a/gems/aws-sdk-core/lib/seahorse/client/block_io.rb
+++ b/gems/aws-sdk-core/lib/seahorse/client/block_io.rb
@@ -11,6 +11,7 @@ def initialize(&block)
       # @return [Integer]
       def write(chunk)
         @block.call(chunk)
+      ensure
         chunk.bytesize.tap { |chunk_size| @size += chunk_size }
       end
 
diff --git a/gems/aws-sdk-core/lib/seahorse/client/plugins/response_target.rb b/gems/aws-sdk-core/lib/seahorse/client/plugins/response_target.rb
index 9e003b74e36..64de371250f 100644
--- a/gems/aws-sdk-core/lib/seahorse/client/plugins/response_target.rb
+++ b/gems/aws-sdk-core/lib/seahorse/client/plugins/response_target.rb
@@ -28,7 +28,13 @@ def call(context)
           def add_event_listeners(context, target)
             handler = self
             context.http_response.on_headers(200..299) do
-              context.http_response.body = handler.send(:io, target)
+              # In a fresh response body will be a StringIO
+              # However, when a request is retried we may have
+              # an existing ManagedFile or BlockIO and those
+              # should be reused.
+              if context.http_response.body.is_a? StringIO
+                context.http_response.body = handler.send(:io, target)
+              end
             end
 
             context.http_response.on_success(200..299) do
@@ -40,15 +46,18 @@ def add_event_listeners(context, target)
 
             context.http_response.on_error do
               body = context.http_response.body
-              File.unlink(body) if ManagedFile === body
+
+              # When using response_target of file we do not want to write
+              # error messages to the file.  So set the body to a new StringIO
+              if body.is_a? ManagedFile
+                File.unlink(body)
+                context.http_response.body = StringIO.new
+              end
+
               # Aws::S3::Encryption::DecryptHandler (with lower priority)
               # has callbacks registered after ResponseTarget::Handler,
               # where http_response.body is an IODecrypter
-              # and has error callbacks handling for it.
-              # Thus avoid early remove of IODecrypter at ResponseTarget::Handler
-              unless context.http_response.body.respond_to?(:io)
-                context.http_response.body = StringIO.new
-              end
+              # and has error callbacks handling for it so no action is required here
             end
           end
 
diff --git a/gems/aws-sdk-s3/lib/aws-sdk-s3/encryption/io_decrypter.rb b/gems/aws-sdk-s3/lib/aws-sdk-s3/encryption/io_decrypter.rb
index 68273738a90..48e0ec26d50 100644
--- a/gems/aws-sdk-s3/lib/aws-sdk-s3/encryption/io_decrypter.rb
+++ b/gems/aws-sdk-s3/lib/aws-sdk-s3/encryption/io_decrypter.rb
@@ -8,7 +8,8 @@ class IODecrypter
         # @param [IO#write] io An IO-like object that responds to `#write`.
         def initialize(cipher, io)
           @cipher = cipher.clone
-          @io = io
+          # Ensure that IO is reset between retries
+          @io = io.tap { |io| io.truncate(0) if io.respond_to?(:truncate) }
         end
 
         # @return [#write]
@@ -23,6 +24,10 @@ def finalize
           @io.write(@cipher.final)
         end
 
+        def size
+          @io.size
+        end
+
       end
     end
   end