diff --git a/careful/bin/check-careful.sh b/careful/bin/check-careful.sh
index 3103289fd..22ed6bac2 100755
--- a/careful/bin/check-careful.sh
+++ b/careful/bin/check-careful.sh
@@ -36,9 +36,13 @@ HAS_SEPARATOR=false
 case "$CMD" in
   # Real separators, plus JSON-escaped newlines (\n / \r) which survive the
   # grep extraction path as literal two-char sequences and still mark a chain.
-  *';'*|*'|'*|*'&'*|*$'\n'*|*$'\r'*|*'\n'*|*'\r'*) HAS_SEPARATOR=true ;;
+  # Command/backtick substitution counts as chaining too: a token like
+  # `$(./wipe-all)/node_modules` ends in a whitelisted suffix while running
+  # anything inside the substitution. Plain $VAR expansion stays allowed —
+  # only `$(` triggers.
+  *';'*|*'|'*|*'&'*|*'$('*|*'`'*|*$'\n'*|*$'\r'*|*'\n'*|*'\r'*) HAS_SEPARATOR=true ;;
 esac
-if [ "$HAS_SEPARATOR" = false ] && printf '%s' "$CMD" | grep -qE 'rm\s+(-[a-zA-Z]*r[a-zA-Z]*\s+|--recursive\s+)' 2>/dev/null; then
+if [ "$HAS_SEPARATOR" = false ] && printf '%s' "$CMD" | grep -qE 'rm\s+(-[a-zA-Z]*[rR][a-zA-Z]*\s+|--recursive\s+)' 2>/dev/null; then
   SAFE_ONLY=true
   RM_ARGS=$(printf '%s' "$CMD" | sed -E 's/.*rm[[:space:]]+(-[a-zA-Z]+[[:space:]]+)*//;s/--recursive[[:space:]]*//')
   for target in $RM_ARGS; do
@@ -63,8 +67,8 @@ fi
 WARN=""
 PATTERN=""
 
-# rm -rf / rm -r / rm --recursive
-if printf '%s' "$CMD" | grep -qE 'rm\s+(-[a-zA-Z]*r|--recursive)' 2>/dev/null; then
+# rm -rf / rm -r / rm -R / rm --recursive (capital -R is BSD/macOS recursive)
+if printf '%s' "$CMD" | grep -qE 'rm\s+(-[a-zA-Z]*[rR]|--recursive)' 2>/dev/null; then
   WARN="Destructive: recursive delete (rm -r). This permanently removes files."
   PATTERN="rm_recursive"
 fi
diff --git a/test/hook-scripts.test.ts b/test/hook-scripts.test.ts
index 5fc70583c..be3c12e34 100644
--- a/test/hook-scripts.test.ts
+++ b/test/hook-scripts.test.ts
@@ -121,6 +121,66 @@ describe('check-careful.sh', () => {
       expect(output.permissionDecision).toBe('ask');
       expect(output.message).toContain('recursive delete');
     });
+
+    // Command substitution is a chaining form: the substitution token can end in
+    // a whitelisted suffix while running anything inside $(...) or backticks,
+    // and the safe-exception early exit would skip ALL downstream checks.
+    test('rm -rf $(./wipe-all)/node_modules warns (command substitution)', () => {
+      const { exitCode, output } = runHook(CAREFUL_SCRIPT, carefulInput('rm -rf $(./wipe-all)/node_modules'));
+      expect(exitCode).toBe(0);
+      expect(output.permissionDecision).toBe('ask');
+      expect(output.message).toContain('recursive delete');
+    });
+
+    test('rm -rf `./wipe-all`/node_modules warns (backtick substitution)', () => {
+      const { exitCode, output } = runHook(CAREFUL_SCRIPT, carefulInput('rm -rf `./wipe-all`/node_modules'));
+      expect(exitCode).toBe(0);
+      expect(output.permissionDecision).toBe('ask');
+      expect(output.message).toContain('recursive delete');
+    });
+
+    // Capital -R is the documented recursive flag on BSD rm (macOS) and accepted
+    // by GNU rm. Both greps previously required a lowercase r, so `rm -R /`
+    // silently allowed.
+    test('rm -R / warns (capital -R recursive)', () => {
+      const { exitCode, output } = runHook(CAREFUL_SCRIPT, carefulInput('rm -R /'));
+      expect(exitCode).toBe(0);
+      expect(output.permissionDecision).toBe('ask');
+      expect(output.message).toContain('recursive delete');
+    });
+
+    test('rm -fR /home/user warns (capital R in flag cluster)', () => {
+      const { exitCode, output } = runHook(CAREFUL_SCRIPT, carefulInput('rm -fR /home/user'));
+      expect(exitCode).toBe(0);
+      expect(output.permissionDecision).toBe('ask');
+      expect(output.message).toContain('recursive delete');
+    });
+
+    test('rm -Rf node_modules allows (capital R, single safe target)', () => {
+      const { exitCode, output } = runHook(CAREFUL_SCRIPT, carefulInput('rm -Rf node_modules'));
+      expect(exitCode).toBe(0);
+      expect(output.permissionDecision).toBeUndefined();
+    });
+
+    // The JSON-escaped-newline separator branch (literal two-char \n surviving
+    // the grep extraction path) had dedicated code but no test exercising it.
+    test('newline-chained rm warns (escaped-newline separator branch)', () => {
+      const { exitCode, output } = runHook(CAREFUL_SCRIPT, carefulInput('rm -rf /etc/x\nrm -rf node_modules'));
+      expect(exitCode).toBe(0);
+      expect(output.permissionDecision).toBe('ask');
+      expect(output.message).toContain('recursive delete');
+    });
+
+    // Deliberate false positive, pinned: a safe-prefix chain ending in a safe rm
+    // is indistinguishable from the dangerous-first exploit shape without real
+    // shell parsing, so warn-on-all-chains is the designed fail-closed direction.
+    // A future per-segment parser must consciously change this test.
+    test('cd app && rm -rf node_modules asks (fail-closed on chains, by design)', () => {
+      const { exitCode, output } = runHook(CAREFUL_SCRIPT, carefulInput('cd app && rm -rf node_modules'));
+      expect(exitCode).toBe(0);
+      expect(output.permissionDecision).toBe('ask');
+      expect(output.message).toContain('recursive delete');
+    });
   });
 
   // --- SQL destructive commands ---