diff --git a/Cargo.lock b/Cargo.lock
index 55802dedd101..846c8605d01a 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -4796,7 +4796,9 @@ dependencies = [
  "reflink-copy",
  "regex",
  "rustc-hash",
+ "same-file",
  "schemars",
+ "self-replace",
  "serde",
  "serde_json",
  "sha2",
diff --git a/Cargo.toml b/Cargo.toml
index 37e8b974f9b6..de26817fef4c 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -144,6 +144,7 @@ rustix = { version = "0.38.37", default-features = false, features = ["fs", "std
 same-file = { version = "1.0.6" }
 schemars = { version = "0.8.21", features = ["url"] }
 seahash = { version = "4.1.0" }
+self-replace = { version = "1.5.0" }
 serde = { version = "1.0.210", features = ["derive"] }
 serde-untagged = { version = "0.1.6" }
 serde_json = { version = "1.0.128" }
diff --git a/crates/uv-install-wheel/Cargo.toml b/crates/uv-install-wheel/Cargo.toml
index d7dcd8fd1db7..9ce308160727 100644
--- a/crates/uv-install-wheel/Cargo.toml
+++ b/crates/uv-install-wheel/Cargo.toml
@@ -52,6 +52,10 @@ tracing = { workspace = true }
 walkdir = { workspace = true }
 zip = { workspace = true }
 
+[target.'cfg(target_os = "windows")'.dependencies]
+same-file = { workspace = true }
+self-replace = { workspace = true }
+
 [dev-dependencies]
 anyhow = { version = "1.0.89" }
 assert_fs = { version = "1.1.2" }
diff --git a/crates/uv-install-wheel/src/uninstall.rs b/crates/uv-install-wheel/src/uninstall.rs
index 15bbdc3f625b..b824bceb9b10 100644
--- a/crates/uv-install-wheel/src/uninstall.rs
+++ b/crates/uv-install-wheel/src/uninstall.rs
@@ -33,10 +33,39 @@ pub fn uninstall_wheel(dist_info: &Path) -> Result<Uninstall, Error> {
     let mut file_count = 0usize;
     let mut dir_count = 0usize;
 
+    #[cfg(windows)]
+    let itself = std::env::current_exe().ok();
+
     // Uninstall the files, keeping track of any directories that are left empty.
     let mut visited = BTreeSet::new();
     for entry in &record {
         let path = site_packages.join(&entry.path);
+
+        // On Windows, deleting the current executable is a special case.
+        #[cfg(windows)]
+        if let Some(itself) = itself.as_ref() {
+            if itself
+                .file_name()
+                .is_some_and(|itself| path.file_name().is_some_and(|path| itself == path))
+            {
+                if same_file::is_same_file(itself, &path).unwrap_or(false) {
+                    tracing::debug!("Detected self-delete of executable: {}", path.display());
+                    match self_replace::self_delete_outside_path(site_packages) {
+                        Ok(()) => {
+                            trace!("Removed file: {}", path.display());
+                            file_count += 1;
+                            if let Some(parent) = path.parent() {
+                                visited.insert(normalize_path(parent));
+                            }
+                        }
+                        Err(err) if err.kind() == std::io::ErrorKind::NotFound => {}
+                        Err(err) => return Err(err.into()),
+                    }
+                    continue;
+                }
+            }
+        }
+
         match fs::remove_file(&path) {
             Ok(()) => {
                 trace!("Removed file: {}", path.display());