diff --git a/src/executor/valgrind/executor.rs b/src/executor/valgrind/executor.rs
index aa28c8c8b..67a726c9a 100644
--- a/src/executor/valgrind/executor.rs
+++ b/src/executor/valgrind/executor.rs
@@ -57,8 +57,9 @@ impl Executor for ValgrindExecutor {
         }
 
         if let Err(error) = venv_compat::symlink_libpython(None) {
-            warn!("Failed to symlink libpython");
-            debug!("Script error: {error}");
+            warn!(
+                "Failed to symlink libpython into the virtual environment, flamegraphs may contain artifacts: {error}"
+            );
         }
 
         Ok(())
diff --git a/src/executor/valgrind/helpers/venv_compat.rs b/src/executor/valgrind/helpers/venv_compat.rs
index d1d6b660b..1aae87769 100644
--- a/src/executor/valgrind/helpers/venv_compat.rs
+++ b/src/executor/valgrind/helpers/venv_compat.rs
@@ -50,6 +50,101 @@ pub fn symlink_libpython(cwd: Option<&String>) -> anyhow::Result<()> {
 #[cfg(test)]
 mod tests {
     use super::*;
+    use std::{fs, os::unix::fs::symlink, path::Path};
+
+    const LIBPYTHON: &str = "libpython3.13.so.1.0";
+
+    fn write_executable(path: &Path, content: &str) {
+        fs::write(path, content).unwrap();
+        fs::set_permissions(path, fs::Permissions::from_mode(0o755)).unwrap();
+    }
+
+    /// Runs the script with a fake `uv` and `ldd` first in `PATH`. `uv python find` reports
+    /// `uv_python`, and `ldd` always reports `LIBPYTHON` as missing.
+    fn run_script(root: &Path, uv_python: &Path) -> std::process::Output {
+        let fake_bin = root.join("fake-bin");
+        fs::create_dir_all(&fake_bin).unwrap();
+        write_executable(
+            &fake_bin.join("uv"),
+            &format!("#!/usr/bin/env bash\necho {}\n", uv_python.display()),
+        );
+        write_executable(
+            &fake_bin.join("ldd"),
+            &format!("#!/usr/bin/env bash\necho '{LIBPYTHON} => not found'\n"),
+        );
+        // Without a `python3` in the fake bin, the script would inspect the host's python.
+        symlink(uv_python, fake_bin.join("python3")).unwrap();
+
+        let path = format!("{}:{}", fake_bin.display(), std::env::var("PATH").unwrap());
+        Command::new("bash")
+            .arg("-c")
+            .arg(VENV_COMPAT_SCRIPT)
+            .env("PATH", path)
+            .output()
+            .unwrap()
+    }
+
+    /// Creates `real/bin/python3` and a `venv/bin/python3` pointing at it.
+    fn create_venv(root: &Path) -> std::path::PathBuf {
+        fs::create_dir_all(root.join("real/bin")).unwrap();
+        fs::create_dir_all(root.join("venv/bin")).unwrap();
+        fs::write(root.join("real/bin/python3"), "").unwrap();
+        fs::write(root.join("venv/pyvenv.cfg"), "").unwrap();
+        symlink(root.join("real/bin/python3"), root.join("venv/bin/python3")).unwrap();
+        root.join("venv/bin/python3")
+    }
+
+    #[test]
+    fn test_creates_missing_lib_dir_and_link() {
+        let dir = tempfile::tempdir().unwrap();
+        let venv_python = create_venv(dir.path());
+
+        let output = run_script(dir.path(), &venv_python);
+
+        assert!(output.status.success(), "{output:?}");
+        let link = dir.path().join("venv/lib").join(LIBPYTHON);
+        assert_eq!(
+            fs::read_link(link).unwrap(),
+            dir.path()
+                .canonicalize()
+                .unwrap()
+                .join("real/lib")
+                .join(LIBPYTHON)
+        );
+    }
+
+    #[test]
+    fn test_replaces_dangling_link() {
+        let dir = tempfile::tempdir().unwrap();
+        let venv_python = create_venv(dir.path());
+        fs::create_dir_all(dir.path().join("venv/lib")).unwrap();
+        let link = dir.path().join("venv/lib").join(LIBPYTHON);
+        symlink(dir.path().join("moved-python/lib").join(LIBPYTHON), &link).unwrap();
+
+        let output = run_script(dir.path(), &venv_python);
+
+        assert!(output.status.success(), "{output:?}");
+        assert_eq!(
+            fs::read_link(link).unwrap(),
+            dir.path()
+                .canonicalize()
+                .unwrap()
+                .join("real/lib")
+                .join(LIBPYTHON)
+        );
+    }
+
+    #[test]
+    fn test_skips_python_outside_a_venv() {
+        let dir = tempfile::tempdir().unwrap();
+        let venv_python = create_venv(dir.path());
+        fs::remove_file(dir.path().join("venv/pyvenv.cfg")).unwrap();
+
+        let output = run_script(dir.path(), &venv_python);
+
+        assert!(output.status.success(), "{output:?}");
+        assert!(!dir.path().join("venv/lib").exists());
+    }
 
     // Only run in Github Actions, to ensure python is dynamically linked.
     #[test_with::env(GITHUB_ACTIONS)]
diff --git a/src/executor/valgrind/helpers/venv_compat.sh b/src/executor/valgrind/helpers/venv_compat.sh
index fb5ac21eb..e4cfbb0b3 100755
--- a/src/executor/valgrind/helpers/venv_compat.sh
+++ b/src/executor/valgrind/helpers/venv_compat.sh
@@ -3,6 +3,14 @@
 function add_symlink() {
     local venv_python="$1"
 
+    venv_path="$(dirname "$(dirname "$venv_python")")"
+    # Only virtual environments resolve libpython relative to themselves; any other Python
+    # (e.g. a uv shim in ~/.local/bin) has nowhere to put the link.
+    if [ ! -f "$venv_path/pyvenv.cfg" ]; then
+        echo "Not a virtual environment, skipping: $venv_python"
+        return 0
+    fi
+
     system_python="$(readlink -f "$venv_python")"
     if [ -z "$system_python" ]; then
         echo "Error: Failed to resolve real path for $venv_python" >&2
@@ -10,7 +18,6 @@ function add_symlink() {
     fi
 
     system_path="$(dirname $(dirname "$system_python"))"
-    venv_path="$(dirname $(dirname "$venv_python"))"
     echo "Python installation (system): $system_path"
     echo "Python installation (venv): $venv_path"
 
@@ -26,13 +33,14 @@ function add_symlink() {
     system_link="$system_path/lib/$libpython_name"
     if [ -e "$venv_link" ]; then
         echo "Symlink already exists: $venv_link"
-    else
-        echo "Creating symlink: $system_link -> $venv_link"
-        ln -s "$system_link" "$venv_link"
-        if [ $? -ne 0 ]; then
-            echo "Error: Failed to create symlink $venv_link" >&2
-            return 1
-        fi
+        return 0
+    fi
+
+    # `-f` replaces a dangling link left behind when the venv's Python was moved or upgraded.
+    echo "Creating symlink: $system_link -> $venv_link"
+    if ! mkdir -p "$venv_path/lib" || ! ln -sfn "$system_link" "$venv_link"; then
+        echo "Error: Failed to create symlink $venv_link" >&2
+        return 1
     fi
 }