diff --git a/CHANGELOG.md b/CHANGELOG.md
index efcb2029a..7bf7fc0ea 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,6 @@
 # Changelog
 
+- **Fixed** Prefix environment assignments like `PATH=... command` now affect executable lookup during task planning, so tools provided only by the prefixed `PATH` can be resolved correctly ([#440](https://github.com/voidzero-dev/vite-task/pull/440))
 - **Changed** Cache misses caused by a tracked env var now name the env var inline, for example `cache miss: env 'NODE_ENV' changed`, instead of the generic `envs changed` message ([#438](https://github.com/voidzero-dev/vite-task/pull/438))
 - **Fixed** The task cache is now stored in a per-schema-version subdirectory (e.g. `node_modules/.vite/task-cache/v13/`), so switching between branches that pin different Vite+ versions no longer fails with `Unrecognized database version`. Each version keeps its own cache directory; a cache from a different version is ignored rather than aborting the run ([#433](https://github.com/voidzero-dev/vite-task/pull/433))
 - **Added** A task's `env` and `untrackedEnv` glob patterns now support `!` negation: a `!`-prefixed pattern excludes matching variables (e.g. `["VITE_*", "!VITE_SECRET"]` tracks every `VITE_*` except `VITE_SECRET`) ([#425](https://github.com/voidzero-dev/vite-task/pull/425))
diff --git a/crates/vite_task_plan/src/plan.rs b/crates/vite_task_plan/src/plan.rs
index 84faa171a..12bf5c334 100644
--- a/crates/vite_task_plan/src/plan.rs
+++ b/crates/vite_task_plan/src/plan.rs
@@ -141,6 +141,15 @@ async fn plan_task_as_execution_node(
                 let mut context = context.duplicate();
                 context.push_stack_frame(task_node_index, add_item_span.clone());
 
+                // This command's env context: extend the planning context with
+                // the command's prefix envs (`FOO=1 tool ...`). Everything that
+                // interprets the command reads this one context — program
+                // lookup, plan-request callbacks, and nested-run planning. The
+                // per-and-item duplicate above scopes the extension to this
+                // command, matching shell semantics (`FOO=1 a && b` does not
+                // set `FOO` for `b`).
+                context.add_envs(and_item.envs.iter());
+
                 let mut args = and_item.args;
                 let extra_args = if is_last_command && and_item_index == and_item_count - 1 {
                     // For the last and_item of the last command, append extra args from the plan context
@@ -247,8 +256,6 @@ async fn plan_task_as_execution_node(
 
                         // Save task name before consuming the request
                         let task_name = query_plan_request.query.task_name.clone();
-                        // Add prefix envs to the context
-                        context.add_envs(and_item.envs.iter());
                         let QueryPlanRequest { query, plan_options } = query_plan_request;
                         let query = Arc::new(query);
                         let nested_plan =
diff --git a/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/package.json b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/package.json
new file mode 100644
index 000000000..372537b0e
--- /dev/null
+++ b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/package.json
@@ -0,0 +1,5 @@
+{
+  "scripts": {
+    "check": "PATH= vtt"
+  }
+}
diff --git a/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots.toml b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots.toml
new file mode 100644
index 000000000..2ed5ce8f0
--- /dev/null
+++ b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots.toml
@@ -0,0 +1,3 @@
+[[plan]]
+name = "prefix_path_hides_tool_binary"
+args = ["run", "check"]
diff --git a/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots/query_prefix_path_hides_tool_binary.snap b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots/query_prefix_path_hides_tool_binary.snap
new file mode 100644
index 000000000..ee075ad18
--- /dev/null
+++ b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots/query_prefix_path_hides_tool_binary.snap
@@ -0,0 +1 @@
+Failed to find executable vtt under cwd <workspace>/ with PATH: : cannot find binary path
\ No newline at end of file
diff --git a/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots/task_graph.jsonc b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots/task_graph.jsonc
new file mode 100644
index 000000000..c898c069b
--- /dev/null
+++ b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/snapshots/task_graph.jsonc
@@ -0,0 +1,44 @@
+// task graph
+[
+  {
+    "key": [
+      "<workspace>/",
+      "check"
+    ],
+    "node": {
+      "task_display": {
+        "package_name": "",
+        "task_name": "check",
+        "package_path": "<workspace>/"
+      },
+      "resolved_config": {
+        "commands": [
+          "PATH= vtt"
+        ],
+        "resolved_options": {
+          "cwd": "<workspace>/",
+          "cache_config": {
+            "env_config": {
+              "fingerprinted_envs": [],
+              "untracked_env": [
+                "<default untracked envs>"
+              ]
+            },
+            "input_config": {
+              "includes_auto": true,
+              "positive_globs": [],
+              "negative_globs": []
+            },
+            "output_config": {
+              "includes_auto": false,
+              "positive_globs": [],
+              "negative_globs": []
+            }
+          }
+        }
+      },
+      "source": "PackageJsonScript"
+    },
+    "neighbors": []
+  }
+]
diff --git a/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/vite-task.json b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/vite-task.json
new file mode 100644
index 000000000..d548edfac
--- /dev/null
+++ b/crates/vite_task_plan/tests/plan_snapshots/fixtures/prefix_env_path_lookup/vite-task.json
@@ -0,0 +1,3 @@
+{
+  "cache": true
+}
diff --git a/crates/vite_task_plan/tests/plan_snapshots/main.rs b/crates/vite_task_plan/tests/plan_snapshots/main.rs
index 72641b404..988152ae4 100644
--- a/crates/vite_task_plan/tests/plan_snapshots/main.rs
+++ b/crates/vite_task_plan/tests/plan_snapshots/main.rs
@@ -193,8 +193,8 @@ fn run_case_inner(
         "folder '{fixture_name}' should be a workspace root"
     );
 
-    let fake_bin_dir = std::path::PathBuf::from(std::env::var_os("CARGO_MANIFEST_DIR").unwrap())
-        .join("tests/plan_snapshots/fake-bin");
+    let manifest_dir = std::path::PathBuf::from(std::env::var_os("CARGO_MANIFEST_DIR").unwrap());
+    let fake_bin_dir = manifest_dir.join("tests/plan_snapshots/fake-bin");
     let combined_path =
         Arc::<OsStr>::from(std::ffi::OsString::from(fake_bin_dir.to_str().unwrap()));
 
diff --git a/crates/vite_task_plan/tests/plan_snapshots/redact.rs b/crates/vite_task_plan/tests/plan_snapshots/redact.rs
index e34702ab1..b0fdd7230 100644
--- a/crates/vite_task_plan/tests/plan_snapshots/redact.rs
+++ b/crates/vite_task_plan/tests/plan_snapshots/redact.rs
@@ -105,8 +105,7 @@ pub fn redact_snapshot(value: &impl Serialize, workspace_root: &str) -> serde_js
         .to_owned();
     let mut json_value = serde_json::to_value(value).unwrap();
 
-    // On Windows, paths might use either backslashes or forward slashes
-    // Try both variants for workspace_root, manifest_dir, and tools_dir
+    // On Windows, paths might use either backslashes or forward slashes.
     let workspace_root_forward = workspace_root.cow_replace('\\', "/");
     let manifest_dir_forward = manifest_dir.as_str().cow_replace('\\', "/");
     let tools_dir_forward = tools_dir_str.as_str().cow_replace('\\', "/");