diff --git a/e2e/shell/test_shims_activate_prepend b/e2e/shell/test_shims_activate_prepend
index 236d9f6694..afac8c9723 100644
--- a/e2e/shell/test_shims_activate_prepend
+++ b/e2e/shell/test_shims_activate_prepend
@@ -14,3 +14,21 @@ assert_contains "env PATH='$CUSTOM_PATH' $MISE_BIN activate bash --shims" "expor
 
 # Shims not in PATH: should also be emitted as a prepend with shims first
 assert_contains "env PATH='/some/other/bin:/usr/bin' $MISE_BIN activate bash --shims" "export PATH=\"$SHIMS_DIR:"
+
+# Regression #10264: when the dir containing the mise executable is already in
+# PATH (e.g. a deb install at /usr/bin), --shims must NOT re-prepend it, which
+# would reorder PATH (moving /usr/bin ahead of /usr/local/bin). Only the shims
+# dir should be prepended, so exactly one `export PATH=` line is emitted.
+EXE_DIR="$(dirname "$MISE_BIN")"
+if ! out="$(env PATH="$EXE_DIR:/usr/local/bin:/usr/bin" "$MISE_BIN" activate bash --shims 2>&1)"; then
+  echo "FAIL: 'mise activate bash --shims' exited non-zero:"
+  printf '%s\n' "$out"
+  exit 1
+fi
+assert_contains_text "$out" "export PATH=\"$SHIMS_DIR:"
+path_lines="$(printf '%s\n' "$out" | grep -c 'export PATH=' || true)"
+if [[ $path_lines != "1" ]]; then
+  echo "FAIL: expected exactly one 'export PATH=' line (shims only) since the mise dir is already in PATH, got $path_lines:"
+  printf '%s\n' "$out"
+  exit 1
+fi
diff --git a/src/cli/activate.rs b/src/cli/activate.rs
index 6b2b6c0ff0..924afc7353 100644
--- a/src/cli/activate.rs
+++ b/src/cli/activate.rs
@@ -102,10 +102,14 @@ impl Activate {
     fn activate_shims(&self, shell: &dyn Shell, mise_bin: &Path) -> std::io::Result<()> {
         let exe_dir = mise_bin.parent().unwrap();
         let mut prelude = vec![];
-        // For shells with native path dedup/reorder (fish), always emit path commands
-        // using MovePrependEnv so entries get moved to front on re-source (e.g. VS Code).
-        // For other shells, keep the is_dir_in_path guard to avoid PATH growth on re-source.
-        if let Some(p) = self.shims_prepend_path(shell, exe_dir) {
+        // The shims dir is always (move-)prepended so it stays at the front of PATH
+        // even when activation is re-sourced (e.g. VS Code terminals) — see #8757.
+        // The mise executable's own dir only needs to be present so `mise` is
+        // callable, so it uses the guarded prepend: this avoids re-prepending (and
+        // thereby reordering) a system dir such as /usr/bin that is already in PATH
+        // for deb/rpm installs, which would otherwise move it ahead of
+        // /usr/local/bin (#10264).
+        if let Some(p) = self.prepend_path(exe_dir) {
             prelude.push(p);
         }
         if let Some(p) = self.shims_prepend_path(shell, &dirs::SHIMS) {
@@ -165,9 +169,10 @@ impl Activate {
         }
     }
 
-    /// Used by activate_shims. Always prepends the path to the front, even if
-    /// already present (accepting a duplicate entry). For shells with native path
-    /// dedup (fish), uses MovePrependEnv to reorder without duplicating.
+    /// Used by activate_shims for the shims directory. Always prepends the path to
+    /// the front, even if already present (accepting a duplicate entry), so the
+    /// shims dir wins on re-source. For shells with native path dedup (fish), uses
+    /// MovePrependEnv to reorder without duplicating.
     fn shims_prepend_path(&self, shell: &dyn Shell, p: &Path) -> Option<ActivatePrelude> {
         if !is_dir_not_in_nix(p) || p.is_relative() {
             return None;