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diff --git a/Inter,Manrope.zip b/Inter,Manrope.zip
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diff --git a/src/server/email-smtp.ts b/src/server/email-smtp.ts
index 85f15be..42c87af 100644
--- a/src/server/email-smtp.ts
+++ b/src/server/email-smtp.ts
@@ -13,6 +13,20 @@ function b64(input: string) {
   return Buffer.from(input, "utf8").toString("base64")
 }
 
+function extractEnvelopeAddress(from: string): string {
+  // Prefer address inside angle brackets
+  const angle = from.match(/<\s*([^>\s]+)\s*>/)
+  if (angle?.[1]) return angle[1]
+  // Fallback: address inside parentheses
+  const paren = from.match(/\(([^)\s]+@[^)\s]+)\)/)
+  if (paren?.[1]) return paren[1]
+  // Fallback: first email-like substring
+  const email = from.match(/[A-Za-z0-9._%+-]+@[A-Za-z0-9.-]+\.[A-Za-z]{2,}/)
+  if (email?.[0]) return email[0]
+  // Last resort: use whole string
+  return from
+}
+
 export async function sendSmtpMail(cfg: SmtpConfig, to: string, subject: string, html: string) {
   return new Promise<void>((resolve, reject) => {
     const socket = tls.connect(cfg.port, cfg.host, { rejectUnauthorized: false }, () => {
@@ -44,7 +58,8 @@ export async function sendSmtpMail(cfg: SmtpConfig, to: string, subject: string,
         await wait(/^334 /)
         send(b64(cfg.password))
         await wait(/^235 /)
-        send(`MAIL FROM:<${cfg.from.match(/<(.+)>/)?.[1] ?? cfg.from}>`)
+        const envelopeFrom = extractEnvelopeAddress(cfg.from)
+        send(`MAIL FROM:<${envelopeFrom}>`)
         await wait(/^250 /)
         send(`RCPT TO:<${to}>`)
         await wait(/^250 /)
diff --git a/tests/email-smtp.test.ts b/tests/email-smtp.test.ts
index f9bc261..93a491c 100644
--- a/tests/email-smtp.test.ts
+++ b/tests/email-smtp.test.ts
@@ -1,6 +1,7 @@
 import { describe, it, expect, vi, beforeEach } from "vitest"
 
 // Mock tls to simulate an SMTP server over implicit TLS
+let lastWrites: string[] = []
 vi.mock("tls", () => {
   class MockSocket {
     listeners: Record<string, Function[]> = {}
@@ -58,6 +59,7 @@ vi.mock("tls", () => {
 
   function connect(_port: number, _host: string, _opts: unknown, cb?: Function) {
     const socket = new MockSocket()
+    lastWrites = socket.writes
     // initial server greeting
     setTimeout(() => {
       cb?.()
@@ -66,7 +68,7 @@ vi.mock("tls", () => {
     return socket as unknown as NodeJS.WritableStream & { on: MockSocket["on"] }
   }
 
-  return { default: { connect }, connect }
+  return { default: { connect }, connect, __getLastWrites: () => lastWrites }
 })
 
 describe("sendSmtpMail", () => {
@@ -87,5 +89,23 @@ describe("sendSmtpMail", () => {
       )
     ).resolves.toBeUndefined()
   })
-})
 
+  it("extracts envelope address from parentheses or raw email", async () => {
+    const { sendSmtpMail } = await import("@/server/email-smtp")
+    const tlsMock = await import("tls" as any)
+    await sendSmtpMail(
+      {
+        host: "smtp.mock",
+        port: 465,
+        username: "user@example.com",
+        password: "secret",
+        from: "Chatwoot chat@esdrasrenan.com.br (chat@esdrasrenan.com.br)",
+      },
+      "rcpt@example.com",
+      "Subject",
+      "<p>Hi</p>"
+    )
+    const writes = (tlsMock as any).__getLastWrites() as string[]
+    expect(writes.some((w) => /MAIL FROM:<chat@esdrasrenan.com.br>\r\n/.test(w))).toBe(true)
+  })
+})