fix(gmail): strip CR/LF from header values before MIME assembly

apps/sim/tools/gmail/utils.test.ts

@@ -9,6 +9,7 @@ import {
   escapeHtml,
   htmlToPlainText,
   plainTextToHtml,
+  sanitizeHeaderValue,
 } from './utils'
 
 function decodeSimpleMessage(encoded: string): string {
@@ -60,6 +61,27 @@ describe('encodeRfc2047', () => {
   })
 })
 
+describe('sanitizeHeaderValue', () => {
+  it('collapses embedded CRLF to a single space', () => {
+    expect(sanitizeHeaderValue('foo\r\nBcc: attacker@example.com')).toBe(
+      'foo Bcc: attacker@example.com'
+    )
+  })
+
+  it('collapses embedded bare LF or CR to a single space', () => {
+    expect(sanitizeHeaderValue('foo\nbar')).toBe('foo bar')
+    expect(sanitizeHeaderValue('foo\rbar')).toBe('foo bar')
+  })
+
+  it('collapses consecutive newlines to a single space', () => {
+    expect(sanitizeHeaderValue('foo\r\n\r\nbar')).toBe('foo bar')
+  })
+
+  it('leaves ordinary values unchanged', () => {
+    expect(sanitizeHeaderValue('a@example.com, b@example.com')).toBe('a@example.com, b@example.com')
+  })
+})
+
 describe('escapeHtml', () => {
   it('escapes the five HTML special characters', () => {
     expect(escapeHtml(`<script>alert("x & y's")</script>`)).toBe(
@@ -167,6 +189,39 @@ describe('buildSimpleEmailMessage', () => {
     expect(decoded).toContain('In-Reply-To: <msg-1@example.com>')
     expect(decoded).toContain('References: <root@example.com> <msg-1@example.com>')
   })
+
+  it('strips embedded CRLF from to/cc/bcc/subject/inReplyTo/references so no extra header line is produced', () => {
+    const injected = 'innocuous\r\nBcc: attacker@example.com'
+    const encoded = buildSimpleEmailMessage({
+      to: injected,
+      cc: injected,
+      bcc: injected,
+      subject: injected,
+      body: 'hello',
+      inReplyTo: injected,
+      references: injected,
+    })
+    const decoded = decodeSimpleMessage(encoded)
+    const lines = decoded.split('\n')
+    const bccLines = lines.filter((line) => line.startsWith('Bcc:'))
+    // Exactly one Bcc header line (the legitimate one), holding the sanitized, single-line value.
+    expect(bccLines).toHaveLength(1)
+    expect(bccLines[0]).toBe('Bcc: innocuous Bcc: attacker@example.com')
+    expect(lines).not.toContain('Bcc: attacker@example.com')
+  })
+
+  it('preserves legitimate ASCII, Unicode, and multi-recipient values unchanged', () => {
+    const encoded = buildSimpleEmailMessage({
+      to: 'a@example.com, b@example.com',
+      cc: 'c@example.com',
+      subject: 'Café meeting 🎉',
+      body: 'hello',
+    })
+    const decoded = decodeSimpleMessage(encoded)
+    expect(decoded).toContain('To: a@example.com, b@example.com')
+    expect(decoded).toContain('Cc: c@example.com')
+    expect(decoded).toContain(`Subject: ${encodeRfc2047('Café meeting 🎉')}`)
+  })
 })
 
 describe('buildMimeMessage', () => {
@@ -199,4 +254,71 @@ describe('buildMimeMessage', () => {
     expect(message).toMatch(/Content-Type: multipart\/alternative; boundary="([^"]+)"/)
     expect(message).not.toContain('multipart/mixed')
   })
+
+  it('strips embedded CRLF from header fields and the attachment filename', () => {
+    const injected = 'innocuous\r\nBcc: attacker@example.com'
+    const message = buildMimeMessage({
+      to: injected,
+      cc: injected,
+      bcc: injected,
+      subject: injected,
+      body: 'hello',
+      inReplyTo: injected,
+      references: injected,
+      attachments: [
+        {
+          filename: injected,
+          mimeType: 'text/plain',
+          content: Buffer.from('hi'),
+        },
+      ],
+    })
+    const lines = message.split('\n')
+    const bccLines = lines.filter((line) => line.startsWith('Bcc:'))
+    expect(bccLines).toHaveLength(1)
+    expect(bccLines[0]).toBe('Bcc: innocuous Bcc: attacker@example.com')
+    expect(lines).not.toContain('Bcc: attacker@example.com')
+    expect(message).toContain(
+      'Content-Disposition: attachment; filename="innocuous Bcc: attacker@example.com"'
+    )
+  })
+
+  it('strips embedded CRLF from the attachment mimeType', () => {
+    const injected = 'text/plain\r\nBcc: attacker@example.com'
+    const message = buildMimeMessage({
+      to: 'a@example.com',
+      body: 'hello',
+      attachments: [
+        {
+          filename: 'note.txt',
+          mimeType: injected,
+          content: Buffer.from('hi'),
+        },
+      ],
+    })
+    const lines = message.split('\n')
+    const bccLines = lines.filter((line) => line.startsWith('Bcc:'))
+    expect(bccLines).toHaveLength(0)
+    expect(message).toContain('Content-Type: text/plain Bcc: attacker@example.com')
+  })
+
+  it('preserves legitimate ASCII, Unicode, and multi-recipient values unchanged', () => {
+    const message = buildMimeMessage({
+      to: 'a@example.com, b@example.com',
+      cc: 'c@example.com',
+      subject: 'Café meeting 🎉',
+      body: 'hello',
+      attachments: [
+        {
+          filename: 'note.txt',
+          mimeType: 'text/plain',
+          content: Buffer.from('hi'),
+        },
+      ],
+    })
+    expect(message).toContain('To: a@example.com, b@example.com')
+    expect(message).toContain('Cc: c@example.com')
+    expect(message).toContain(`Subject: ${encodeRfc2047('Café meeting 🎉')}`)
+    expect(message).toContain('Content-Disposition: attachment; filename="note.txt"')
+  })
 })

apps/sim/tools/gmail/utils.ts

@@ -309,6 +309,13 @@ export function encodeRfc2047(value: string): string {
   return `=?UTF-8?B?${Buffer.from(value, 'utf-8').toString('base64')}?=`
 }
 
+/**
+ * Strips CR/LF so a value can't introduce extra lines when placed into a MIME header.
+ */
+export function sanitizeHeaderValue(value: string): string {
+  return value.replace(/[\r\n]+/g, ' ')
+}
+
 /**
  * Encode string or buffer to base64url format (URL-safe base64)
  * Gmail API requires base64url encoding for the raw message field
@@ -432,20 +439,23 @@ export function buildSimpleEmailMessage(params: {
   const boundary = generateBoundary()
   const { plain, html } = buildBodyAlternatives(body, contentType)
 
-  const emailHeaders = ['MIME-Version: 1.0', `To: ${to}`]
+  const emailHeaders = ['MIME-Version: 1.0', `To: ${sanitizeHeaderValue(to)}`]
 
   if (cc) {
-    emailHeaders.push(`Cc: ${cc}`)
+    emailHeaders.push(`Cc: ${sanitizeHeaderValue(cc)}`)
   }
   if (bcc) {
-    emailHeaders.push(`Bcc: ${bcc}`)
+    emailHeaders.push(`Bcc: ${sanitizeHeaderValue(bcc)}`)
   }
 
-  emailHeaders.push(`Subject: ${encodeRfc2047(subject || '')}`)
+  emailHeaders.push(`Subject: ${encodeRfc2047(sanitizeHeaderValue(subject || ''))}`)
 
   if (inReplyTo) {
-    emailHeaders.push(`In-Reply-To: ${inReplyTo}`)
-    const referencesChain = references ? `${references} ${inReplyTo}` : inReplyTo
+    const sanitizedInReplyTo = sanitizeHeaderValue(inReplyTo)
+    emailHeaders.push(`In-Reply-To: ${sanitizedInReplyTo}`)
+    const referencesChain = references
+      ? `${sanitizeHeaderValue(references)} ${sanitizedInReplyTo}`
+      : sanitizedInReplyTo
     emailHeaders.push(`References: ${referencesChain}`)
   }
 
@@ -483,23 +493,28 @@ export function buildMimeMessage(params: BuildMimeMessageParams): string {
   const messageParts: string[] = []
   const { plain, html } = buildBodyAlternatives(body, contentType)
 
-  messageParts.push(`To: ${to}`)
+  messageParts.push(`To: ${sanitizeHeaderValue(to)}`)
   if (cc) {
-    messageParts.push(`Cc: ${cc}`)
+    messageParts.push(`Cc: ${sanitizeHeaderValue(cc)}`)
   }
   if (bcc) {
-    messageParts.push(`Bcc: ${bcc}`)
+    messageParts.push(`Bcc: ${sanitizeHeaderValue(bcc)}`)
   }
-  messageParts.push(`Subject: ${encodeRfc2047(subject || '')}`)
+  messageParts.push(`Subject: ${encodeRfc2047(sanitizeHeaderValue(subject || ''))}`)
 
-  if (inReplyTo) {
-    messageParts.push(`In-Reply-To: ${inReplyTo}`)
+  const sanitizedInReplyTo = inReplyTo ? sanitizeHeaderValue(inReplyTo) : undefined
+  const sanitizedReferences = references ? sanitizeHeaderValue(references) : undefined
+
+  if (sanitizedInReplyTo) {
+    messageParts.push(`In-Reply-To: ${sanitizedInReplyTo}`)
   }
-  if (references) {
-    const referencesChain = inReplyTo ? `${references} ${inReplyTo}` : references
+  if (sanitizedReferences) {
+    const referencesChain = sanitizedInReplyTo
+      ? `${sanitizedReferences} ${sanitizedInReplyTo}`
+      : sanitizedReferences
     messageParts.push(`References: ${referencesChain}`)
-  } else if (inReplyTo) {
-    messageParts.push(`References: ${inReplyTo}`)
+  } else if (sanitizedInReplyTo) {
+    messageParts.push(`References: ${sanitizedInReplyTo}`)
   }
 
   messageParts.push('MIME-Version: 1.0')
@@ -518,8 +533,10 @@ export function buildMimeMessage(params: BuildMimeMessageParams): string {
 
     for (const attachment of attachments) {
       messageParts.push(`--${mixedBoundary}`)
-      messageParts.push(`Content-Type: ${attachment.mimeType}`)
-      messageParts.push(`Content-Disposition: attachment; filename="${attachment.filename}"`)
+      messageParts.push(`Content-Type: ${sanitizeHeaderValue(attachment.mimeType)}`)
+      messageParts.push(
+        `Content-Disposition: attachment; filename="${sanitizeHeaderValue(attachment.filename)}"`
+      )
       messageParts.push('Content-Transfer-Encoding: base64')
       messageParts.push('')