diff --git a/scripts/src/apply-patch-v2.ts b/scripts/src/apply-patch-v2.ts
index 465050de..fca0c65d 100644
--- a/scripts/src/apply-patch-v2.ts
+++ b/scripts/src/apply-patch-v2.ts
@@ -115,6 +115,37 @@ export function applyPatchV2HelpPayload() {
       firstLine: beginMarker,
       lastLine: endMarker
     },
+    rules: [
+      "Add File has no @@ hunk marker: put content immediately after `*** Add File: <path>` and prefix every content line with +.",
+      "A blank line in Add File is a line containing only +.",
+      "Update File uses @@ or @@ context markers, followed by context lines starting with space and changed lines starting with - or +.",
+      "Prefer `trans <route> apply-patch < /tmp/patch.diff` for long patches, Windows paths, or quoting-sensitive content."
+    ],
+    examples: {
+      addFile: [
+        beginMarker,
+        `${addFileMarker}path/to/new.txt`,
+        "+first line",
+        "+",
+        "+third line after a blank line",
+        endMarker
+      ].join("\n"),
+      updateFile: [
+        beginMarker,
+        `${updateFileMarker}path/to/existing.txt`,
+        emptyChangeContextMarker,
+        " context line",
+        "-old line",
+        "+new line",
+        " more context",
+        endMarker
+      ].join("\n")
+    },
+    commonPitfalls: [
+      "Do not put @@ after `*** Add File:`; @@ is only for Update File.",
+      "Do not paste unified diff headers such as `@@ -1,3 +1,4 @@`.",
+      "Do not use remote Python/Perl/sed heredocs for text patches when `trans <route> apply-patch` is available."
+    ],
     note: "apply-patch reads patch text from stdin and uses the v2 engine by default. Use `apply-patch-v1` only for the legacy helper."
   };
 }
@@ -148,7 +179,7 @@ export function parseApplyPatchV2(patchText: string): PatchParseResult {
       while (index < lines.length - 1 && !isFileHeader(lines[index] ?? "")) {
         const addLine = lines[index] ?? "";
         if (!addLine.startsWith("+")) {
-          throw new ApplyPatchV2Error("invalid add file line; every added line must start with +", { line: index + 1, path: filePath });
+          throw invalidAddFileLineError(addLine, index + 1, filePath);
         }
         added.push(addLine.slice(1));
         index += 1;
@@ -189,6 +220,26 @@ export function parseApplyPatchV2(patchText: string): PatchParseResult {
   return { patch, hunks };
 }
 
+function invalidAddFileLineError(lineText: string, line: number, filePath: string): ApplyPatchV2Error {
+  const details = { line, path: filePath, text: lineText };
+  if (lineText.trimStart().startsWith("@@")) {
+    return new ApplyPatchV2Error(
+      "invalid add file line: remove @@ for Add File. Add File sections do not use hunk markers; put content directly after the header and prefix every content line with +.",
+      details,
+    );
+  }
+  if (lineText.trim().length === 0) {
+    return new ApplyPatchV2Error(
+      "invalid add file line: blank lines in Add File must be written as a line containing only +.",
+      details,
+    );
+  }
+  return new ApplyPatchV2Error(
+    "invalid add file line: every Add File content line must start with +. Add File has no @@ marker; use @@ only under Update File.",
+    details,
+  );
+}
+
 export function deriveUpdatedContent(filePath: string, originalContent: string, chunks: UpdateChunk[]): PatchUpdateResult {
   const originalLines = splitContentLines(originalContent);
   const replacements = computeReplacements(filePath, originalLines, chunks);
diff --git a/scripts/ssh-argv-guidance-contract-test.ts b/scripts/ssh-argv-guidance-contract-test.ts
index 3b35f554..e695a689 100644
--- a/scripts/ssh-argv-guidance-contract-test.ts
+++ b/scripts/ssh-argv-guidance-contract-test.ts
@@ -905,6 +905,24 @@ export async function runSshArgvGuidanceContract(): Promise<JsonRecord> {
   assertCondition(addBeforeFailedUpdateV2.files.hwpod?.includes("device-pod-cli.mjs"), "v2 should preserve an earlier Add File from a large patch when a later hunk misses", addBeforeFailedUpdateV2);
   assertCondition(addBeforeFailedUpdateV2.files["scripts/artifact-publish.mjs"] === "actual artifact line\n", "v2 must leave the failed later file unchanged", addBeforeFailedUpdateV2);
 
+  const addFileWithHunkMarkerV2 = await applyPatchV2FixtureAttempt([
+    "*** Begin Patch",
+    "*** Add File: bad-add.txt",
+    "@@",
+    "+content",
+    "*** End Patch",
+    "",
+  ].join("\n"), {}, { stderrOutput: true });
+  assertCondition(addFileWithHunkMarkerV2.exitCode === 1 && addFileWithHunkMarkerV2.error === null, "v2 CLI path should return a visible parse error for Add File @@ misuse", addFileWithHunkMarkerV2);
+  assertCondition(addFileWithHunkMarkerV2.stdout === "", "v2 Add File parse failures should keep Codex-style empty stdout", addFileWithHunkMarkerV2);
+  assertCondition(
+    addFileWithHunkMarkerV2.stderr.includes("remove @@ for Add File")
+      && addFileWithHunkMarkerV2.stderr.includes("prefix every content line with +"),
+    "v2 Add File @@ misuse should tell agents exactly how to repair the patch",
+    addFileWithHunkMarkerV2.stderr,
+  );
+  assertCondition(!addFileWithHunkMarkerV2.commands.some((command) => command.startsWith("write-b64") || command.startsWith("delete")), "v2 Add File parse failures must not touch remote files", addFileWithHunkMarkerV2.commands);
+
   const sequentialCompoundV2 = await applyPatchV2Fixture([
     "*** Begin Patch",
     "*** Update File: sequence.txt",