diff --git a/pkg/plugins/plugin_test.go b/pkg/plugins/plugin_test.go
index 837e63a16..7c8e2ad88 100644
--- a/pkg/plugins/plugin_test.go
+++ b/pkg/plugins/plugin_test.go
@@ -24,7 +24,7 @@ func TestInstall(t *testing.T) {
 	config := &TestConfig{}
 	config.InitConfig()
 	manifestContent, _ := os.ReadFile("./test_artifacts/plugins.toml")
-	testServers := setUpServers(t, manifestContent)
+	testServers := setUpServers(t, manifestContent, nil)
 
 	plugin, _ := LookUpPlugin(context.Background(), config, fs, "appA")
 	err := plugin.Install(context.Background(), config, fs, "2.0.1", testServers.StripeServer.URL)
@@ -42,7 +42,7 @@ func TestInstallFailsIfChecksumCouldNotBeFound(t *testing.T) {
 	config := &TestConfig{}
 	config.InitConfig()
 	manifestContent, _ := os.ReadFile("./test_artifacts/plugins.toml")
-	testServers := setUpServers(t, manifestContent)
+	testServers := setUpServers(t, manifestContent, nil)
 
 	plugin, _ := LookUpPlugin(context.Background(), config, fs, "appA")
 	err := plugin.Install(context.Background(), config, fs, "0.0.0", testServers.StripeServer.URL)
@@ -62,7 +62,7 @@ func TestInstallationFailsIfChecksumDoesNotMatch(t *testing.T) {
 	config := &TestConfig{}
 	config.InitConfig()
 	manifestContent, _ := os.ReadFile("./test_artifacts/plugins.toml")
-	testServers := setUpServers(t, manifestContent)
+	testServers := setUpServers(t, manifestContent, nil)
 
 	plugin, _ := LookUpPlugin(context.Background(), config, fs, "appB")
 	err := plugin.Install(context.Background(), config, fs, "1.2.1", testServers.StripeServer.URL)
@@ -82,7 +82,7 @@ func TestInstallCleansOtherVersionsOfPlugin(t *testing.T) {
 	config := &TestConfig{}
 	config.InitConfig()
 	manifestContent, _ := os.ReadFile("./test_artifacts/plugins.toml")
-	testServers := setUpServers(t, manifestContent)
+	testServers := setUpServers(t, manifestContent, nil)
 
 	// Download plugin version 0.0.1
 	plugin, _ := LookUpPlugin(context.Background(), config, fs, "appA")
@@ -111,7 +111,7 @@ func TestInstallDoesNotCleanIfInstallFails(t *testing.T) {
 	config := &TestConfig{}
 	config.InitConfig()
 	manifestContent, _ := os.ReadFile("./test_artifacts/plugins.toml")
-	testServers := setUpServers(t, manifestContent)
+	testServers := setUpServers(t, manifestContent, nil)
 
 	// Download valid plugin
 	plugin, _ := LookUpPlugin(context.Background(), config, fs, "appA")
@@ -138,7 +138,7 @@ func TestUninstall(t *testing.T) {
 	config := &TestConfig{}
 	config.InitConfig()
 	manifestContent, _ := os.ReadFile("./test_artifacts/plugins.toml")
-	testServers := setUpServers(t, manifestContent)
+	testServers := setUpServers(t, manifestContent, nil)
 
 	// install a plugin to be uninstalled
 	plugin, _ := LookUpPlugin(context.Background(), config, fs, "appA")
diff --git a/pkg/plugins/test_artifacts/plugins-2-merged-foo-1.toml b/pkg/plugins/test_artifacts/plugins-2-merged-foo-1.toml
new file mode 100644
index 000000000..5c64f5a5f
--- /dev/null
+++ b/pkg/plugins/test_artifacts/plugins-2-merged-foo-1.toml
@@ -0,0 +1,134 @@
+[[Plugin]]
+  Shortname = "appA"
+  Binary = "stripe-cli-app-a"
+  MagicCookieValue = "0337A75A-C3C4-4DCF-A9EF-E7A144E5A291"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+[[Plugin]]
+  Shortname = "appB"
+  Binary = "stripe-cli-app-b"
+  MagicCookieValue = "FDBE6FB9-A149-44BD-9639-4D33D8B594E8"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+[[Plugin]]
+  Shortname = "foo"
+  Binary = "stripe-cli-foo"
+  MagicCookieValue = "6C5CFD81-F43C-447B-BBCF-803FF31CD3D1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.2"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.2"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
diff --git a/pkg/plugins/test_artifacts/plugins-2.toml b/pkg/plugins/test_artifacts/plugins-2.toml
new file mode 100644
index 000000000..f41496873
--- /dev/null
+++ b/pkg/plugins/test_artifacts/plugins-2.toml
@@ -0,0 +1,126 @@
+# This is a made up manifest file for unit test purposes.
+# The checksums are the same for all OS versions of a single release for testing simplicity
+# The checksums for appA were generated to match the response returned in the test servers (see ../test_utils.go)
+# The checksums for appB do not match the actual contents returned from the test server.
+[[Plugin]]
+  Shortname = "appA"
+  Binary = "stripe-cli-app-a"
+  MagicCookieValue = "0337A75A-C3C4-4DCF-A9EF-E7A144E5A291"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+[[Plugin]]
+  Shortname = "appB"
+  Binary = "stripe-cli-app-b"
+  MagicCookieValue = "FDBE6FB9-A149-44BD-9639-4D33D8B594E8"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+[[Plugin]]
+  Shortname = "foo"
+  Binary = "stripe-cli-foo"
+  MagicCookieValue = "6C5CFD81-F43C-447B-BBCF-803FF31CD3D1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
diff --git a/pkg/plugins/test_artifacts/plugins-3-merged-foo-1.toml b/pkg/plugins/test_artifacts/plugins-3-merged-foo-1.toml
new file mode 100644
index 000000000..c12e5b89d
--- /dev/null
+++ b/pkg/plugins/test_artifacts/plugins-3-merged-foo-1.toml
@@ -0,0 +1,146 @@
+[[Plugin]]
+  Shortname = "appA"
+  Binary = "stripe-cli-app-a"
+  MagicCookieValue = "0337A75A-C3C4-4DCF-A9EF-E7A144E5A291"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+[[Plugin]]
+  Shortname = "appB"
+  Binary = "stripe-cli-app-b"
+  MagicCookieValue = "FDBE6FB9-A149-44BD-9639-4D33D8B594E8"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+[[Plugin]]
+  Shortname = "foo"
+  Binary = "stripe-cli-foo"
+  MagicCookieValue = "6C5CFD81-F43C-447B-BBCF-803FF31CD3D1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.2"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.2"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.3"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.3"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
diff --git a/pkg/plugins/test_artifacts/plugins-3.toml b/pkg/plugins/test_artifacts/plugins-3.toml
new file mode 100644
index 000000000..d0998ee36
--- /dev/null
+++ b/pkg/plugins/test_artifacts/plugins-3.toml
@@ -0,0 +1,138 @@
+# This is a made up manifest file for unit test purposes.
+# The checksums are the same for all OS versions of a single release for testing simplicity
+# The checksums for appA were generated to match the response returned in the test servers (see ../test_utils.go)
+# The checksums for appB do not match the actual contents returned from the test server.
+[[Plugin]]
+  Shortname = "appA"
+  Binary = "stripe-cli-app-a"
+  MagicCookieValue = "0337A75A-C3C4-4DCF-A9EF-E7A144E5A291"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+[[Plugin]]
+  Shortname = "appB"
+  Binary = "stripe-cli-app-b"
+  MagicCookieValue = "FDBE6FB9-A149-44BD-9639-4D33D8B594E8"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+[[Plugin]]
+  Shortname = "foo"
+  Binary = "stripe-cli-foo"
+  MagicCookieValue = "6C5CFD81-F43C-447B-BBCF-803FF31CD3D1"
+
+[[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.3"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.3"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
diff --git a/pkg/plugins/test_artifacts/plugins-foo-1.toml b/pkg/plugins/test_artifacts/plugins-foo-1.toml
new file mode 100644
index 000000000..2d7def851
--- /dev/null
+++ b/pkg/plugins/test_artifacts/plugins-foo-1.toml
@@ -0,0 +1,18 @@
+# This is a made up manifest file for unit test purposes.
+# The checksums are the same for all OS versions of a single release for testing simplicity
+[[Plugin]]
+  Shortname = "foo"
+  Binary = "stripe-cli-foo"
+  MagicCookieValue = "6C5CFD81-F43C-447B-BBCF-803FF31CD3D1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.2"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.2"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
diff --git a/pkg/plugins/test_artifacts/plugins-merged-foo-1.toml b/pkg/plugins/test_artifacts/plugins-merged-foo-1.toml
new file mode 100644
index 000000000..aa8c7352d
--- /dev/null
+++ b/pkg/plugins/test_artifacts/plugins-merged-foo-1.toml
@@ -0,0 +1,122 @@
+[[Plugin]]
+  Shortname = "appA"
+  Binary = "stripe-cli-app-a"
+  MagicCookieValue = "0337A75A-C3C4-4DCF-A9EF-E7A144E5A291"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "0.0.1"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.0.1"
+    Sum = "3c909ec628b7d32536a65fd15545db527a7509e734995d4ef4806694fbd89c3a"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "2.0.1"
+    Sum = "3752e4e3a9f1b17f85b542b355893b8614ad8662a3fb8eba6ebed66d1f9e2a87"
+
+[[Plugin]]
+  Shortname = "appB"
+  Binary = "stripe-cli-app-b"
+  MagicCookieValue = "FDBE6FB9-A149-44BD-9639-4D33D8B594E8"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "linux"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "windows"
+    Version = "1.2.1"
+    Sum = "2f05d4b689d270cafb02285f35f44866f7dc8a2d368a3f9d1124373eeab31fb1"
+
+[[Plugin]]
+  Shortname = "foo"
+  Binary = "stripe-cli-foo"
+  MagicCookieValue = "6C5CFD81-F43C-447B-BBCF-803FF31CD3D1"
+
+  [[Plugin.Release]]
+    Arch = "amd64"
+    OS = "darwin"
+    Version = "0.0.2"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
+
+  [[Plugin.Release]]
+    Arch = "arm64"
+    OS = "darwin"
+    Version = "0.0.2"
+    Sum = "125653c37803a51a048f6687f7f66d511be614f675f199cd6c71928b74875238"
diff --git a/pkg/plugins/test_utils.go b/pkg/plugins/test_utils.go
index e9263bd5d..82b871108 100644
--- a/pkg/plugins/test_utils.go
+++ b/pkg/plugins/test_utils.go
@@ -1,7 +1,7 @@
 package plugins
 
 import (
-	"fmt"
+	"encoding/json"
 	"net/http"
 	"net/http/httptest"
 	"os"
@@ -11,6 +11,7 @@ import (
 	"github.com/spf13/afero"
 
 	"github.com/stripe/stripe-cli/pkg/config"
+	"github.com/stripe/stripe-cli/pkg/requests"
 )
 
 // TestConfig Implementations out several methods
@@ -64,11 +65,18 @@ func (ts *TestServers) CloseAll() {
 }
 
 // setUpServers sets up a local stripe server and artifactory server for unit tests
-func setUpServers(t *testing.T, manifestContent []byte) TestServers {
+func setUpServers(t *testing.T, manifestContent []byte, additionalManifests map[string][]byte) TestServers {
+	additionalManifestNames := []string{}
+	for name := range additionalManifests {
+		additionalManifestNames = append(additionalManifestNames, name)
+	}
+
 	artifactoryServer := httptest.NewServer(http.HandlerFunc(func(res http.ResponseWriter, req *http.Request) {
 		switch url := req.URL.String(); {
 		case url == "/plugins.toml":
 			res.Write(manifestContent)
+		case contains(additionalManifestNames, strings.TrimPrefix(url, "/")):
+			res.Write(additionalManifests[strings.TrimPrefix(url, "/")])
 		case strings.Contains(url, "/appA/2.0.1"):
 			res.Write([]byte("hello, I am appA_2.0.1"))
 		case strings.Contains(url, "/appA/1.0.1"):
@@ -90,7 +98,15 @@ func setUpServers(t *testing.T, manifestContent []byte) TestServers {
 	stripeServer := httptest.NewServer(http.HandlerFunc(func(res http.ResponseWriter, req *http.Request) {
 		switch url := req.URL.String(); url {
 		case "/v1/stripecli/get-plugin-url":
-			res.Write([]byte(fmt.Sprintf(`{"base_url": "%s"}`, artifactoryServer.URL)))
+			pd := requests.PluginData{
+				PluginBaseURL:       artifactoryServer.URL,
+				AdditionalManifests: additionalManifestNames,
+			}
+			body, err := json.Marshal(pd)
+			if err != nil {
+				t.Error(err)
+			}
+			res.Write(body)
 		default:
 			t.Errorf("Received an unexpected request URL: %s", req.URL.String())
 		}
@@ -101,3 +117,12 @@ func setUpServers(t *testing.T, manifestContent []byte) TestServers {
 		StripeServer:      stripeServer,
 	}
 }
+
+func contains(sl []string, str string) bool {
+	for _, s := range sl {
+		if s == str {
+			return true
+		}
+	}
+	return false
+}
diff --git a/pkg/plugins/utilities.go b/pkg/plugins/utilities.go
index 08a9090ad..c824de4ac 100644
--- a/pkg/plugins/utilities.go
+++ b/pkg/plugins/utilities.go
@@ -12,6 +12,7 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
+	"sort"
 	"strings"
 
 	log "github.com/sirupsen/logrus"
@@ -113,20 +114,20 @@ func RefreshPluginManifest(ctx context.Context, config config.IConfig, fs afero.
 		return err
 	}
 
-	pluginManifestURL := fmt.Sprintf("%s/%s", pluginData.PluginBaseURL, "plugins.toml")
-	body, err := FetchRemoteResource(pluginManifestURL)
+	pluginList, err := fetchAndMergeManifests(pluginData)
 	if err != nil {
 		return err
 	}
 
-	if err := validatePluginManifest(body); err != nil {
-		return err
-	}
-
 	configPath := config.GetConfigFolder(os.Getenv("XDG_CONFIG_HOME"))
 	pluginManifestPath := filepath.Join(configPath, "plugins.toml")
 
-	err = afero.WriteFile(fs, pluginManifestPath, body, 0644)
+	body := new(bytes.Buffer)
+	if err := toml.NewEncoder(body).Encode(pluginList); err != nil {
+		return err
+	}
+
+	err = afero.WriteFile(fs, pluginManifestPath, body.Bytes(), 0644)
 
 	if err != nil {
 		return err
@@ -135,16 +136,77 @@ func RefreshPluginManifest(ctx context.Context, config config.IConfig, fs afero.
 	return nil
 }
 
-func validatePluginManifest(body []byte) error {
+func fetchAndMergeManifests(pluginData requests.PluginData) (*PluginList, error) {
+	pluginList, err := fetchPluginList(pluginData.PluginBaseURL, "plugins.toml")
+	if err != nil {
+		return nil, err
+	}
+
+	additionalPluginLists := []*PluginList{}
+	for _, filename := range pluginData.AdditionalManifests {
+		additionalPluginList, err := fetchPluginList(pluginData.PluginBaseURL, filename)
+		if err != nil {
+			return nil, err
+		}
+		additionalPluginLists = append(additionalPluginLists, additionalPluginList)
+	}
+
+	mergePluginLists(pluginList, additionalPluginLists)
+
+	return pluginList, nil
+}
+
+func fetchPluginList(baseURL, manifestFilename string) (*PluginList, error) {
+	pluginManifestURL := fmt.Sprintf("%s/%s", baseURL, manifestFilename)
+	body, err := FetchRemoteResource(pluginManifestURL)
+	if err != nil {
+		return nil, err
+	}
+	return validatePluginManifest(body)
+}
+
+func validatePluginManifest(body []byte) (*PluginList, error) {
 	var manifestBody PluginList
 
 	if err := toml.Unmarshal(body, &manifestBody); err != nil {
-		return fmt.Errorf("Received an invalid plugin manifest. Error: %s", err)
+		return nil, fmt.Errorf("Received an invalid plugin manifest. Error: %s", err)
 	}
 	if len(manifestBody.Plugins) == 0 {
-		return fmt.Errorf("Received an empty plugin manifest")
+		return nil, fmt.Errorf("Received an empty plugin manifest")
 	}
-	return nil
+	return &manifestBody, nil
+}
+
+// mergePluginLists merges additional plugin lists into the main plugin list, in place
+func mergePluginLists(pluginList *PluginList, additionalPluginLists []*PluginList) {
+	for _, list := range additionalPluginLists {
+		for _, pl := range list.Plugins {
+			addPluginToList(pluginList, pl)
+		}
+	}
+}
+
+func addPluginToList(pluginList *PluginList, pl Plugin) {
+	idx := findPluginIndex(pluginList, pl)
+	if idx == -1 {
+		pluginList.Plugins = append(pluginList.Plugins, pl)
+	} else {
+		pluginList.Plugins[idx].Releases = append(pluginList.Plugins[idx].Releases, pl.Releases...)
+
+		// Other code assumes the releases are sorted with latest version last.
+		sort.Slice(pluginList.Plugins[idx].Releases, func(i, j int) bool {
+			return pluginList.Plugins[idx].Releases[i].Version < pluginList.Plugins[idx].Releases[j].Version
+		})
+	}
+}
+
+func findPluginIndex(list *PluginList, p Plugin) int {
+	for i, pp := range list.Plugins {
+		if pp.MagicCookieValue == p.MagicCookieValue {
+			return i
+		}
+	}
+	return -1
 }
 
 // AddEntryToPluginManifest update plugins.toml with a new release version
@@ -247,6 +309,10 @@ func FetchRemoteResource(url string) ([]byte, error) {
 		return nil, err
 	}
 
+	if resp.StatusCode == http.StatusNotFound {
+		return nil, fmt.Errorf("remote resource not found: url=%s", url)
+	}
+
 	defer resp.Body.Close()
 
 	body, err := io.ReadAll(resp.Body)
diff --git a/pkg/plugins/utilities_test.go b/pkg/plugins/utilities_test.go
index d23361a2c..6145fb0d6 100644
--- a/pkg/plugins/utilities_test.go
+++ b/pkg/plugins/utilities_test.go
@@ -5,6 +5,7 @@ import (
 	"os"
 	"testing"
 
+	"github.com/BurntSushi/toml"
 	"github.com/spf13/afero"
 	"github.com/spf13/cobra"
 	"github.com/stretchr/testify/require"
@@ -49,7 +50,7 @@ func TestRefreshPluginManifest(t *testing.T) {
 	config := &TestConfig{}
 	config.InitConfig()
 	updatedManifestContent, _ := os.ReadFile("./test_artifacts/plugins_updated.toml")
-	testServers := setUpServers(t, updatedManifestContent)
+	testServers := setUpServers(t, updatedManifestContent, nil)
 	defer func() { testServers.CloseAll() }()
 
 	err := RefreshPluginManifest(context.Background(), config, fs, testServers.StripeServer.URL)
@@ -58,7 +59,115 @@ func TestRefreshPluginManifest(t *testing.T) {
 	// We expect the /plugins.toml file in the test fs is updated
 	pluginManifestContent, err := afero.ReadFile(fs, "/plugins.toml")
 	require.Nil(t, err)
-	require.Equal(t, updatedManifestContent, pluginManifestContent)
+
+	actualPluginList := PluginList{}
+	err = toml.Unmarshal(pluginManifestContent, &actualPluginList)
+	require.Nil(t, err)
+
+	expectedPluginList := PluginList{}
+	err = toml.Unmarshal(updatedManifestContent, &expectedPluginList)
+	require.Nil(t, err)
+
+	require.Equal(t, expectedPluginList, actualPluginList)
+}
+
+func TestRefreshPluginManifestMergesAdditionalManifest(t *testing.T) {
+	fs := setUpFS()
+	config := &TestConfig{}
+	config.InitConfig()
+	manifestContent, _ := os.ReadFile("./test_artifacts/plugins.toml")
+	mergedManifestContent, _ := os.ReadFile("./test_artifacts/plugins-merged-foo-1.toml")
+
+	fooManifest, _ := os.ReadFile("./test_artifacts/plugins-foo-1.toml")
+	additionalManifests := map[string][]byte{
+		"plugins-foo-1.toml": fooManifest,
+	}
+
+	testServers := setUpServers(t, manifestContent, additionalManifests)
+	defer func() { testServers.CloseAll() }()
+
+	err := RefreshPluginManifest(context.Background(), config, fs, testServers.StripeServer.URL)
+	require.Nil(t, err)
+
+	// We expect the /plugins.toml file in the test fs is updated
+	pluginManifestContent, err := afero.ReadFile(fs, "/plugins.toml")
+	require.Nil(t, err)
+
+	actualPluginList := PluginList{}
+	err = toml.Unmarshal(pluginManifestContent, &actualPluginList)
+	require.Nil(t, err)
+
+	expectedPluginList := PluginList{}
+	err = toml.Unmarshal(mergedManifestContent, &expectedPluginList)
+	require.Nil(t, err)
+
+	require.Equal(t, expectedPluginList, actualPluginList)
+}
+
+func TestRefreshPluginManifestMergesExisitingPlugin(t *testing.T) {
+	fs := setUpFS()
+	config := &TestConfig{}
+	config.InitConfig()
+	manifestContent, _ := os.ReadFile("./test_artifacts/plugins-2.toml")
+	mergedManifestContent, _ := os.ReadFile("./test_artifacts/plugins-2-merged-foo-1.toml")
+
+	fooManifest, _ := os.ReadFile("./test_artifacts/plugins-foo-1.toml")
+	additionalManifests := map[string][]byte{
+		"plugins-foo-1.toml": fooManifest,
+	}
+
+	testServers := setUpServers(t, manifestContent, additionalManifests)
+	defer func() { testServers.CloseAll() }()
+
+	err := RefreshPluginManifest(context.Background(), config, fs, testServers.StripeServer.URL)
+	require.Nil(t, err)
+
+	// We expect the /plugins.toml file in the test fs is updated
+	pluginManifestContent, err := afero.ReadFile(fs, "/plugins.toml")
+	require.Nil(t, err)
+
+	actualPluginList := PluginList{}
+	err = toml.Unmarshal(pluginManifestContent, &actualPluginList)
+	require.Nil(t, err)
+
+	expectedPluginList := PluginList{}
+	err = toml.Unmarshal(mergedManifestContent, &expectedPluginList)
+	require.Nil(t, err)
+
+	require.Equal(t, expectedPluginList, actualPluginList)
+}
+
+func TestRefreshPluginManifestSortsPluginReleases(t *testing.T) {
+	fs := setUpFS()
+	config := &TestConfig{}
+	config.InitConfig()
+	manifestContent, _ := os.ReadFile("./test_artifacts/plugins-3.toml")
+	mergedManifestContent, _ := os.ReadFile("./test_artifacts/plugins-3-merged-foo-1.toml")
+
+	fooManifest, _ := os.ReadFile("./test_artifacts/plugins-foo-1.toml")
+	additionalManifests := map[string][]byte{
+		"plugins-foo-1.toml": fooManifest,
+	}
+
+	testServers := setUpServers(t, manifestContent, additionalManifests)
+	defer func() { testServers.CloseAll() }()
+
+	err := RefreshPluginManifest(context.Background(), config, fs, testServers.StripeServer.URL)
+	require.Nil(t, err)
+
+	// We expect the /plugins.toml file in the test fs is updated
+	pluginManifestContent, err := afero.ReadFile(fs, "/plugins.toml")
+	require.Nil(t, err)
+
+	actualPluginList := PluginList{}
+	err = toml.Unmarshal(pluginManifestContent, &actualPluginList)
+	require.Nil(t, err)
+
+	expectedPluginList := PluginList{}
+	err = toml.Unmarshal(mergedManifestContent, &expectedPluginList)
+	require.Nil(t, err)
+
+	require.Equal(t, expectedPluginList, actualPluginList)
 }
 
 func TestRefreshPluginManifestFailsInvalidManifest(t *testing.T) {
@@ -66,7 +175,7 @@ func TestRefreshPluginManifestFailsInvalidManifest(t *testing.T) {
 	config := &TestConfig{}
 	config.InitConfig()
 	emptyManifestContent := []byte{}
-	testServers := setUpServers(t, emptyManifestContent)
+	testServers := setUpServers(t, emptyManifestContent, nil)
 	defer func() { testServers.CloseAll() }()
 
 	err := RefreshPluginManifest(context.Background(), config, fs, testServers.StripeServer.URL)
diff --git a/pkg/requests/plugin.go b/pkg/requests/plugin.go
index 1d05e94e2..a279b7d0d 100644
--- a/pkg/requests/plugin.go
+++ b/pkg/requests/plugin.go
@@ -10,7 +10,8 @@ import (
 
 // PluginData contains the plugin download information
 type PluginData struct {
-	PluginBaseURL string `json:"base_url"`
+	PluginBaseURL       string   `json:"base_url"`
+	AdditionalManifests []string `json:"additional_manifests,omitempty"`
 }
 
 // GetPluginData returns the plugin download information