diff --git a/v2/robotmk/src/bin/scheduler/results.rs b/v2/robotmk/src/bin/scheduler/results.rs
index e2104228..9e0d03a1 100644
--- a/v2/robotmk/src/bin/scheduler/results.rs
+++ b/v2/robotmk/src/bin/scheduler/results.rs
@@ -28,6 +28,7 @@ impl WriteSection for SchedulerPhase {
 #[derive(Serialize)]
 pub struct RCCSetupFailures {
     pub telemetry_disabling: Vec<String>,
+    pub long_path_support: Vec<String>,
     pub shared_holotree: Vec<String>,
     pub holotree_init: Vec<String>,
 }
diff --git a/v2/robotmk/src/bin/scheduler/setup/rcc.rs b/v2/robotmk/src/bin/scheduler/setup/rcc.rs
index 5cfa2305..7d98367c 100644
--- a/v2/robotmk/src/bin/scheduler/setup/rcc.rs
+++ b/v2/robotmk/src/bin/scheduler/setup/rcc.rs
@@ -53,6 +53,7 @@ fn rcc_setup_working_directory(working_directory: &Utf8Path) -> Utf8PathBuf {
 fn rcc_setup(global_config: &GlobalConfig, rcc_suites: Vec<Suite>) -> Result<Vec<Suite>> {
     let mut rcc_setup_failures = RCCSetupFailures {
         telemetry_disabling: vec![],
+        long_path_support: vec![],
         shared_holotree: vec![],
         holotree_init: vec![],
     };
@@ -64,11 +65,24 @@ fn rcc_setup(global_config: &GlobalConfig, rcc_suites: Vec<Suite>) -> Result<Vec
         failed_suites.into_iter().map(|suite| suite.name).collect();
     if !rcc_setup_failures.telemetry_disabling.is_empty() {
         error!(
-            "Dropping the following suites due RCC telemetry disabling failure: {}",
+            "Dropping the following suites due to RCC telemetry disabling failure: {}",
             rcc_setup_failures.telemetry_disabling.join(", ")
         );
     }
 
+    debug!("Enabling support for long paths");
+    let (sucessful_suites, failed_suites) =
+        enable_long_path_support(global_config, sucessful_suites)
+            .context("Enabling support for long paths failed")?;
+    rcc_setup_failures.long_path_support =
+        failed_suites.into_iter().map(|suite| suite.name).collect();
+    if !rcc_setup_failures.long_path_support.is_empty() {
+        error!(
+            "Dropping the following suites due to long path support enabling failure: {}",
+            rcc_setup_failures.long_path_support.join(", ")
+        );
+    }
+
     debug!("Initializing shared holotree");
     let (sucessful_suites, failed_suites) = shared_holotree_init(global_config, sucessful_suites)
         .context("Shared holotree initialization failed")?;
@@ -115,7 +129,22 @@ fn disable_rcc_telemetry(
                 "--do-not-track".into(),
             ],
         },
-        "rcc_telemetry_disabling",
+        "telemetry_disabling",
+    )
+}
+
+fn enable_long_path_support(
+    global_config: &GlobalConfig,
+    suites: Vec<Suite>,
+) -> Result<(Vec<Suite>, Vec<Suite>)> {
+    run_command_spec_once_in_current_session(
+        global_config,
+        suites,
+        &CommandSpec {
+            executable: global_config.rcc_binary_path.to_string(),
+            arguments: vec!["configure".into(), "longpaths".into(), "--enable".into()],
+        },
+        "long_path_support_enabling",
     )
 }
 
@@ -123,38 +152,19 @@ fn shared_holotree_init(
     global_config: &GlobalConfig,
     suites: Vec<Suite>,
 ) -> Result<(Vec<Suite>, Vec<Suite>)> {
-    Ok(
-        if run_command_spec_in_session(
-            &Session::Current(CurrentSession {}),
-            &RunSpec {
-                id: "rcc_shared_holotree_init",
-                command_spec: &CommandSpec {
-                    executable: global_config.rcc_binary_path.to_string(),
-                    arguments: vec![
-                        "holotree".into(),
-                        "shared".into(),
-                        "--enable".into(),
-                        "--once".into(),
-                    ],
-                },
-                base_path: &rcc_setup_working_directory(&global_config.working_directory)
-                    .join("shared_holotree_init"),
-                timeout: 120,
-                termination_flag: &global_config.termination_flag,
-            },
-        )? {
-            (suites, vec![])
-        } else {
-            error!(
-            "Shared holotree initialization failed for the following suites which will now be dropped: {}",
-            suites
-                .iter()
-                .map(|suite| suite.name.as_str())
-                .collect::<Vec<&str>>()
-                .join(", ")
-        );
-            (vec![], suites)
+    run_command_spec_once_in_current_session(
+        global_config,
+        suites,
+        &CommandSpec {
+            executable: global_config.rcc_binary_path.to_string(),
+            arguments: vec![
+                "holotree".into(),
+                "shared".into(),
+                "--enable".into(),
+                "--once".into(),
+            ],
         },
+        "shared_holotree_init",
     )
 }
 
@@ -173,6 +183,30 @@ fn holotree_init(
     )
 }
 
+fn run_command_spec_once_in_current_session(
+    global_config: &GlobalConfig,
+    suites: Vec<Suite>,
+    command_spec: &CommandSpec,
+    id: &str,
+) -> Result<(Vec<Suite>, Vec<Suite>)> {
+    Ok(
+        if run_command_spec_in_session(
+            &Session::Current(CurrentSession {}),
+            &RunSpec {
+                id: &format!("robotmk_{id}"),
+                command_spec,
+                base_path: &rcc_setup_working_directory(&global_config.working_directory).join(id),
+                timeout: 120,
+                termination_flag: &global_config.termination_flag,
+            },
+        )? {
+            (suites, vec![])
+        } else {
+            (vec![], suites)
+        },
+    )
+}
+
 fn run_command_spec_per_session(
     global_config: &GlobalConfig,
     suites: Vec<Suite>,