diff --git a/tools/shell-content-rules.mjs b/tools/shell-content-rules.mjs
index 4dfaef54..b1e79dd1 100644
--- a/tools/shell-content-rules.mjs
+++ b/tools/shell-content-rules.mjs
@@ -59,7 +59,34 @@ export function matchAny(patterns, str) {
 
 export function extractPathArgs(tokens) {
   if (!Array.isArray(tokens)) return [];
-  return tokens.slice(1).filter((t) => typeof t === 'string' && !t.startsWith('-') && t !== '>' && t !== '>>');
+  const out = [];
+  for (let i = 1; i < tokens.length; i++) {
+    const t = tokens[i];
+    if (typeof t !== 'string') continue;
+    if (t === '>' || t === '>>' || t === '<' || t === '|') continue;
+    // --flag=VALUE form
+    if (t.startsWith('-')) {
+      const eq = t.indexOf('=');
+      if (eq > 0) {
+        const v = t.slice(eq + 1);
+        if (v && !looksLikeUrl(v)) out.push(v);
+      }
+      continue;
+    }
+    // key=value form (dd-style)
+    const kv = t.match(/^([a-zA-Z_][\w-]*)=(.+)$/);
+    if (kv) {
+      const v = kv[2];
+      if (v && !looksLikeUrl(v)) out.push(v);
+      continue;
+    }
+    if (!looksLikeUrl(t)) out.push(t);
+  }
+  return out;
+}
+
+function looksLikeUrl(s) {
+  return /^https?:\/\//i.test(s) || /^ftp:\/\//i.test(s) || /^ssh:\/\//i.test(s);
 }
 
 export function pathDenyOverlay({
diff --git a/tools/shell-content-rules.test.mjs b/tools/shell-content-rules.test.mjs
index 5fc3d1b3..ecb7e658 100644
--- a/tools/shell-content-rules.test.mjs
+++ b/tools/shell-content-rules.test.mjs
@@ -59,6 +59,30 @@ describe('extractPathArgs', () => {
   });
 });
 
+describe('extractPathArgs edge cases (Stream H Task 2)', () => {
+  it('extracts path from --output=PATH form', () => {
+    expect(extractPathArgs(['curl', '--output=~/.claude/projects/secret.jsonl', 'http://x'])).toContain('~/.claude/projects/secret.jsonl');
+  });
+  it('extracts path from --output PATH form (separate token)', () => {
+    expect(extractPathArgs(['curl', '--output', '~/.claude/projects/secret.jsonl', 'http://x'])).toContain('~/.claude/projects/secret.jsonl');
+  });
+  it('extracts path from dd of=PATH form', () => {
+    expect(extractPathArgs(['dd', 'if=/dev/zero', 'of=~/.claude/projects/x.jsonl'])).toContain('~/.claude/projects/x.jsonl');
+  });
+  it('extracts path from tee PATH (second positional)', () => {
+    expect(extractPathArgs(['tee', '~/.claude/projects/x.jsonl'])).toContain('~/.claude/projects/x.jsonl');
+  });
+  it('extracts path from cp SRC DST (both positionals)', () => {
+    const got = extractPathArgs(['cp', '/tmp/x', '~/.claude/projects/x.jsonl']);
+    expect(got).toContain('~/.claude/projects/x.jsonl');
+  });
+  it('does not include URL as path (heuristic)', () => {
+    const got = extractPathArgs(['curl', '--output', '/tmp/x', 'https://example.com/y']);
+    expect(got).toContain('/tmp/x');
+    expect(got).not.toContain('https://example.com/y');
+  });
+});
+
 describe('pathDenyOverlay', () => {
   it('blocks when a candidate path is protected', () => {
     const r = pathDenyOverlay({ candidatePaths: ['~/.claude/runtime/x.json'] });