diff --git a/tests/integration/_cases/monitors/monitors-run.trycmd b/tests/integration/_cases/monitors/not_windows/monitors-run.trycmd
similarity index 100%
rename from tests/integration/_cases/monitors/monitors-run.trycmd
rename to tests/integration/_cases/monitors/not_windows/monitors-run.trycmd
diff --git a/tests/integration/_cases/monitors/monitors-run-server-error-win.trycmd b/tests/integration/_cases/monitors/server_error/monitors-run-server-error-win.trycmd
similarity index 100%
rename from tests/integration/_cases/monitors/monitors-run-server-error-win.trycmd
rename to tests/integration/_cases/monitors/server_error/monitors-run-server-error-win.trycmd
diff --git a/tests/integration/_cases/monitors/monitors-run-server-error.trycmd b/tests/integration/_cases/monitors/server_error/monitors-run-server-error.trycmd
similarity index 100%
rename from tests/integration/_cases/monitors/monitors-run-server-error.trycmd
rename to tests/integration/_cases/monitors/server_error/monitors-run-server-error.trycmd
diff --git a/tests/integration/_cases/monitors/monitors-run-win.trycmd b/tests/integration/_cases/monitors/windows/monitors-run-win.trycmd
similarity index 100%
rename from tests/integration/_cases/monitors/monitors-run-win.trycmd
rename to tests/integration/_cases/monitors/windows/monitors-run-win.trycmd
diff --git a/tests/integration/monitors.rs b/tests/integration/monitors.rs
new file mode 100644
index 0000000000..6fc8129da8
--- /dev/null
+++ b/tests/integration/monitors.rs
@@ -0,0 +1,34 @@
+use crate::integration::{mock_endpoint, register_test, EndpointOptions};
+
+#[test]
+fn command_monitors() {
+    let _list_endpoint = mock_endpoint(
+        EndpointOptions::new("GET", "/api/0/organizations/wat-org/monitors/?cursor=", 200)
+            .with_response_file("monitors/get-monitors.json"),
+    );
+    let _envelope_endpoint =
+        mock_endpoint(EndpointOptions::new("POST", "/api/1337/envelope/", 200));
+    let _token_endpoint = mock_endpoint(
+        EndpointOptions::new("POST", "/api/0/monitors/foo-monitor/checkins/", 200)
+            .with_response_file("monitors/post-monitors.json"),
+    );
+
+    let cases = register_test("monitors/*.trycmd");
+
+    #[cfg(not(windows))]
+    cases.case("tests/integration/_cases/monitors/not_windows/*.trycmd");
+
+    #[cfg(windows)]
+    cases.case("tests/integration/_cases/monitors/windows/*.trycmd");
+}
+
+#[test]
+fn command_monitors_run_server_error() {
+    let _server = mock_endpoint(EndpointOptions::new("POST", "/api/1337/envelope/", 500));
+
+    #[cfg(not(windows))]
+    register_test("monitors/server_error/monitors-run-server-error.trycmd");
+
+    #[cfg(windows)]
+    register_test("monitors/server_error/monitors-run-server-error-win.trycmd");
+}
diff --git a/tests/integration/monitors/list.rs b/tests/integration/monitors/list.rs
deleted file mode 100644
index 4399eb6923..0000000000
--- a/tests/integration/monitors/list.rs
+++ /dev/null
@@ -1,15 +0,0 @@
-use crate::integration::{mock_endpoint, register_test, EndpointOptions};
-
-#[test]
-fn command_monitors_list() {
-    let _server = mock_endpoint(
-        EndpointOptions::new("GET", "/api/0/organizations/wat-org/monitors/?cursor=", 200)
-            .with_response_file("monitors/get-monitors.json"),
-    );
-    register_test("monitors/monitors-list.trycmd");
-}
-
-#[test]
-fn command_monitors_list_help() {
-    register_test("monitors/monitors-list-help.trycmd");
-}
diff --git a/tests/integration/monitors/mod.rs b/tests/integration/monitors/mod.rs
deleted file mode 100644
index c13e754e7e..0000000000
--- a/tests/integration/monitors/mod.rs
+++ /dev/null
@@ -1,14 +0,0 @@
-use crate::integration::register_test;
-
-mod list;
-mod run;
-
-#[test]
-fn command_monitors_help() {
-    register_test("monitors/monitors-help.trycmd");
-}
-
-#[test]
-fn command_monitors_no_subcommand() {
-    register_test("monitors/monitors-no-subcommand.trycmd");
-}
diff --git a/tests/integration/monitors/run.rs b/tests/integration/monitors/run.rs
deleted file mode 100644
index 64bffcabc8..0000000000
--- a/tests/integration/monitors/run.rs
+++ /dev/null
@@ -1,50 +0,0 @@
-use crate::integration::{self, EndpointOptions};
-
-#[test]
-fn command_monitors_run() {
-    let _server =
-        integration::mock_endpoint(EndpointOptions::new("POST", "/api/1337/envelope/", 200));
-    if cfg!(windows) {
-        integration::register_test("monitors/monitors-run-win.trycmd");
-    } else {
-        integration::register_test("monitors/monitors-run.trycmd");
-    }
-}
-
-#[test]
-fn command_monitors_run_server_error() {
-    let _server =
-        integration::mock_endpoint(EndpointOptions::new("POST", "/api/1337/envelope/", 500));
-
-    #[cfg(not(windows))]
-    integration::register_test("monitors/monitors-run-server-error.trycmd");
-
-    #[cfg(windows)]
-    integration::register_test("monitors/monitors-run-server-error-win.trycmd");
-}
-
-#[test]
-fn command_monitors_run_osenv() {
-    let _server =
-        integration::mock_endpoint(EndpointOptions::new("POST", "/api/1337/envelope/", 200));
-    integration::register_test("monitors/monitors-run-osenv.trycmd");
-}
-
-#[test]
-fn command_monitors_run_environment() {
-    let _server =
-        integration::mock_endpoint(EndpointOptions::new("POST", "/api/1337/envelope/", 200));
-    integration::register_test("monitors/monitors-run-environment.trycmd");
-}
-
-#[test]
-fn command_monitors_run_environment_long() {
-    let _server =
-        integration::mock_endpoint(EndpointOptions::new("POST", "/api/1337/envelope/", 200));
-    integration::register_test("monitors/monitors-run-environment-long.trycmd");
-}
-
-#[test]
-fn command_monitors_run_help() {
-    integration::register_test("monitors/monitors-run-help.trycmd");
-}