diff --git a/src/core/auto-approval/__tests__/commands.spec.ts b/src/core/auto-approval/__tests__/commands.spec.ts
new file mode 100644
index 0000000000..d7264f7062
--- /dev/null
+++ b/src/core/auto-approval/__tests__/commands.spec.ts
@@ -0,0 +1,32 @@
+import { containsDangerousSubstitution, getCommandDecision } from "../commands"
+
+describe("containsDangerousSubstitution()", () => {
+	it("does not flag Python assignment grouping '=(' inside heredoc content", () => {
+		const cmd = [
+			"python - <<'PY'",
+			"import json, pathlib",
+			"data = {'notes': ''}",
+			"data['notes']=(data.get('notes','')+'; policy set to linked-only by user').lstrip('; ')",
+			"print(data['notes'])",
+			"PY",
+		].join("\n")
+
+		expect(containsDangerousSubstitution(cmd)).toBe(false)
+	})
+
+	it("does not flag simple assignment grouping pattern x=(...)", () => {
+		expect(containsDangerousSubstitution("x=(1+2)")).toBe(false)
+	})
+
+	it("does flag zsh process substitution when used as an argument", () => {
+		expect(containsDangerousSubstitution("cat =(echo hi)")).toBe(true)
+	})
+})
+
+describe("getCommandDecision()", () => {
+	it("auto-approves allowed heredoc command when no dangerous substitution is present", () => {
+		const cmd = ["python - <<'PY'", "x=(1+2)", "print(x)", "PY"].join("\n")
+
+		expect(getCommandDecision(cmd, ["python"], [])).toBe("auto_approve")
+	})
+})
diff --git a/src/core/auto-approval/commands.ts b/src/core/auto-approval/commands.ts
index 83a80cab0f..f22fc52f32 100644
--- a/src/core/auto-approval/commands.ts
+++ b/src/core/auto-approval/commands.ts
@@ -46,7 +46,9 @@ export function containsDangerousSubstitution(source: string): boolean {
 
 	// Check for zsh process substitution =(...) which executes commands
 	// =(...) creates a temporary file containing the output of the command, but executes it
-	const zshProcessSubstitution = /=\([^)]+\)/.test(source)
+	// Only match when preceded by whitespace or command separators (argument position),
+	// not when preceded by identifiers/brackets (assignment position like x=(...) or data['key']=(...))
+	const zshProcessSubstitution = /(^|[\s&|;])=\([^)]+\)/.test(source)
 
 	// Check for zsh glob qualifiers with code execution (e:...:)
 	// Patterns like *(e:whoami:) or ?(e:rm -rf /:) execute commands during glob expansion
diff --git a/src/shared/parse-command.ts b/src/shared/parse-command.ts
index a8d87b76ac..06ab305ea2 100644
--- a/src/shared/parse-command.ts
+++ b/src/shared/parse-command.ts
@@ -2,6 +2,30 @@ import { parse } from "shell-quote"
 
 export type ShellToken = string | { op: string } | { command: string }
 
+type HeredocStart = {
+	delimiter: string
+	stripLeadingTabs: boolean
+}
+
+function parseHeredocStart(line: string): HeredocStart | null {
+	// Matches:
+	// - <<EOF
+	// - <<'EOF'
+	// - <<"EOF"
+	// - <<-EOF  (strip leading tabs in terminator line)
+	//
+	// Notes:
+	// - Intentionally minimal: supports common heredoc forms used in Roo tool commands.
+	// - Delimiter is restricted to [A-Za-z0-9_] to avoid overly broad matches.
+	const match = line.match(/<<(-)?\s*(?:'([A-Za-z0-9_]+)'|"([A-Za-z0-9_]+)"|([A-Za-z0-9_]+))/)
+	if (!match) return null
+
+	return {
+		stripLeadingTabs: match[1] === "-",
+		delimiter: match[2] ?? match[3] ?? match[4] ?? "",
+	}
+}
+
 /**
  * Split a command string into individual sub-commands by
  * chaining operators (&&, ||, ;, |, or &) and newlines.
@@ -23,13 +47,35 @@ export function parseCommand(command: string): string[] {
 	const lines = command.split(/\r\n|\r|\n/)
 	const allCommands: string[] = []
 
-	for (const line of lines) {
+	for (let i = 0; i < lines.length; i++) {
+		const line = lines[i]
 		// Skip empty lines
 		if (!line.trim()) {
 			continue
 		}
 
-		// Process each line through the existing parsing logic
+		// If this line starts a heredoc, treat the entire heredoc block as a single command.
+		// The heredoc body lines are not shell commands and should not affect command approval.
+		const heredocStart = parseHeredocStart(line)
+		if (heredocStart) {
+			const blockLines: string[] = [line]
+			const { delimiter, stripLeadingTabs } = heredocStart
+
+			for (i = i + 1; i < lines.length; i++) {
+				const bodyLine = lines[i]
+				blockLines.push(bodyLine)
+
+				const compareLine = stripLeadingTabs ? bodyLine.replace(/^\t+/, "") : bodyLine
+				if (compareLine.trimEnd() === delimiter) {
+					break
+				}
+			}
+
+			allCommands.push(blockLines.join("\n"))
+			continue
+		}
+
+		// Process each non-heredoc line through the existing parsing logic
 		const lineCommands = parseCommandLine(line)
 		allCommands.push(...lineCommands)
 	}