diff --git a/tooling/xtask/src/tasks/workflows/extension_tests.rs b/tooling/xtask/src/tasks/workflows/extension_tests.rs
index d266a73e1737d6e1d29f278f2646442ccc93a870..44f335ebb68167f1f3ed60d6660dcfddffe4e545 100644
--- a/tooling/xtask/src/tasks/workflows/extension_tests.rs
+++ b/tooling/xtask/src/tasks/workflows/extension_tests.rs
@@ -30,8 +30,8 @@ pub(crate) fn extension_tests() -> Workflow {
 
     let jobs = [
         orchestrate,
-        should_check_rust.and_always().guard(check_rust()),
-        should_check_extension.and_always().guard(check_extension()),
+        should_check_rust.and_always().then(check_rust()),
+        should_check_extension.and_always().then(check_extension()),
     ];
 
     let tests_pass = tests_pass(&jobs, &[]);
diff --git a/tooling/xtask/src/tasks/workflows/run_tests.rs b/tooling/xtask/src/tasks/workflows/run_tests.rs
index d6d9cbd1a9be5db158f4367fac28a8c1a80c0d75..29692f9040e3d7ddb0973552e2ee11089e13d472 100644
--- a/tooling/xtask/src/tasks/workflows/run_tests.rs
+++ b/tooling/xtask/src/tasks/workflows/run_tests.rs
@@ -50,40 +50,38 @@ pub(crate) fn run_tests() -> Workflow {
         check_style(),
         should_run_tests
             .and_not_in_merge_queue()
-            .guard(clippy(Platform::Windows, None)),
+            .then(clippy(Platform::Windows, None)),
         should_run_tests
             .and_always()
-            .guard(clippy(Platform::Linux, None)),
+            .then(clippy(Platform::Linux, None)),
         should_run_tests
             .and_not_in_merge_queue()
-            .guard(clippy(Platform::Mac, None)),
+            .then(clippy(Platform::Mac, None)),
         should_run_tests
             .and_not_in_merge_queue()
-            .guard(clippy(Platform::Mac, Some(Arch::X86_64))),
+            .then(clippy(Platform::Mac, Some(Arch::X86_64))),
         should_run_tests
             .and_not_in_merge_queue()
-            .guard(run_platform_tests(Platform::Windows)),
+            .then(run_platform_tests(Platform::Windows)),
         should_run_tests
             .and_not_in_merge_queue()
-            .guard(run_platform_tests(Platform::Linux)),
+            .then(run_platform_tests(Platform::Linux)),
         should_run_tests
             .and_not_in_merge_queue()
-            .guard(run_platform_tests(Platform::Mac)),
-        should_run_tests.and_not_in_merge_queue().guard(doctests()),
+            .then(run_platform_tests(Platform::Mac)),
+        should_run_tests.and_not_in_merge_queue().then(doctests()),
         should_run_tests
             .and_not_in_merge_queue()
-            .guard(check_workspace_binaries()),
+            .then(check_workspace_binaries()),
+        should_run_tests.and_not_in_merge_queue().then(check_wasm()),
         should_run_tests
             .and_not_in_merge_queue()
-            .guard(check_wasm()),
-        should_run_tests
-            .and_not_in_merge_queue()
-            .guard(check_dependencies()), // could be more specific here?
-        should_check_docs.and_always().guard(check_docs()),
+            .then(check_dependencies()), // could be more specific here?
+        should_check_docs.and_always().then(check_docs()),
         should_check_licences
             .and_not_in_merge_queue()
-            .guard(check_licenses()),
-        should_check_scripts.and_always().guard(check_scripts()),
+            .then(check_licenses()),
+        should_check_scripts.and_always().then(check_scripts()),
     ];
     let ext_tests = extension_tests();
     let tests_pass = tests_pass(&jobs, &[&ext_tests.name]);
@@ -92,7 +90,7 @@ pub(crate) fn run_tests() -> Workflow {
     jobs.push(
         should_run_tests
             .and_always()
-            .guard(check_postgres_and_protobuf_migrations()),
+            .then(check_postgres_and_protobuf_migrations()),
     ); // could be more specific here?
 
     named::workflow()
diff --git a/tooling/xtask/src/tasks/workflows/vars.rs b/tooling/xtask/src/tasks/workflows/vars.rs
index e936f9f8c74ce07f63bead4a65436d481e077777..89c0c4774a634115f02859c7c2557c9da5180f6b 100644
--- a/tooling/xtask/src/tasks/workflows/vars.rs
+++ b/tooling/xtask/src/tasks/workflows/vars.rs
@@ -152,7 +152,7 @@ pub struct PathContextCondition<'a> {
 }
 
 impl<'a> PathContextCondition<'a> {
-    pub fn guard(&'a self, job: NamedJob) -> NamedJob {
+    pub fn then(&'a self, job: NamedJob) -> NamedJob {
         let set_by_step = self
             .condition
             .set_by_step