diff --git a/README.adoc b/README.adoc
index 51084431..02ae1052 100644
--- a/README.adoc
+++ b/README.adoc
@@ -138,6 +138,8 @@ bin/setup
 
 == Upgrade
 
+‼️ If upgrading to Terminus 0.55.0 or higher, please make sure to run the `bin/exchangize` script to upgrade your extensions to use exchanges so you can manage multiple HTTP requests/responses. _You only need to do this once_. ‼️
+
 To upgrade this project for local development, run:
 
 [source,bash]
diff --git a/app/aspects/extensions/upgrader.rb b/app/aspects/extensions/upgrader.rb
new file mode 100644
index 00000000..70540255
--- /dev/null
+++ b/app/aspects/extensions/upgrader.rb
@@ -0,0 +1,36 @@
+# frozen_string_literal: true
+
+require "refinements/hash"
+
+module Terminus
+  module Aspects
+    module Extensions
+      # Automates upgrading poll extensions to use exchanges.
+      class Upgrader
+        include Deps[
+          :logger,
+          extension_repository: "repositories.extension",
+          exchange_repository: "repositories.extension_exchange"
+        ]
+
+        using Refinements::Hash
+
+        def call
+          extension_repository.where(kind: "poll").each do |extension|
+            create_exchange extension
+            logger.info { "Upgraded extension: #{extension.id}." }
+          end
+        end
+
+        def create_exchange extension
+          attributes = extension.to_h
+                                .slice(:headers, :verb, :uris, :body)
+                                .transform_keys!(uris: :template)
+                                .transform_value!(:template) { it.join "\n" }
+
+          exchange_repository.create extension_id: extension.id, **attributes
+        end
+      end
+    end
+  end
+end
diff --git a/bin/exchangize b/bin/exchangize
new file mode 100755
index 00000000..5bbf8016
--- /dev/null
+++ b/bin/exchangize
@@ -0,0 +1,9 @@
+#! /usr/bin/env ruby
+# frozen_string_literal: true
+
+require "bundler/setup"
+Bundler.require :tools
+
+require "hanami/prepare"
+
+Hanami.app["aspects.extensions.upgrader"].call
diff --git a/spec/app/aspects/extensions/upgrader_spec.rb b/spec/app/aspects/extensions/upgrader_spec.rb
new file mode 100644
index 00000000..328a4f3e
--- /dev/null
+++ b/spec/app/aspects/extensions/upgrader_spec.rb
@@ -0,0 +1,60 @@
+# frozen_string_literal: true
+
+require "hanami_helper"
+
+RSpec.describe Terminus::Aspects::Extensions::Upgrader, :db do
+  subject(:upgrader) { described_class.new }
+
+  include_context "with application dependencies"
+
+  let :extension do
+    Factory[
+      :extension,
+      headers: {accept: "application/json"},
+      verb: "post",
+      uris: %w[https://test.io/1 https://test.io/2],
+      body: {sort: :desc}
+    ]
+  end
+
+  let(:repository) { Terminus::Repositories::ExtensionExchange.new }
+
+  describe "#call" do
+    it "adds extension exchanges" do
+      extension
+      upgrader.call
+
+      expect(repository.all.map(&:to_h)).to match(
+        [
+          hash_including(
+            headers: {"accept" => "application/json"},
+            verb: "post",
+            template: "https://test.io/1\nhttps://test.io/2",
+            body: {"sort" => "desc"}
+          )
+        ]
+      )
+    end
+
+    it "logs info" do
+      extension
+      upgrader.call
+      expect(logger.reread).to match(/INFO.+Upgraded extension: #{extension.id}/)
+    end
+  end
+
+  context "with non-poll extensions" do
+    before do
+      Factory[:extension, kind: "static"]
+      upgrader.call
+    end
+
+    it "adds extension exchanges" do
+      expect(repository.all).to eq([])
+    end
+
+    it "logs info" do
+      expect(logger.reread).not_to match(/INFO.+Upgraded extension/)
+    end
+  end
+end