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hensin ni syorui wo tenpusite, kigen made ni okutte.

返信へんしん　に　書類しょるい　を　添付てんぷして、　期限きげん　まで　に　送おくって。hensin ni syorui wo tenpusite, kigen made ni okutte.
Attach the document to your reply and send it by the deadline.
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Questions & Answers about hensin ni syorui wo tenpusite, kigen made ni okutte.

What does the particle に in 返信に do? Why not 返信で?

X に Y を添付する means “attach Y to X.” Here, 返信に marks the target something is attached to: attach the documents to the reply.

  • 返信に 書類を 添付する = attach documents to the reply.
  • 返信で means “by/with (means), in the reply,” and pairs more naturally with verbs like 送る:
    • 返信で 書類を 送る = send the documents in/with your reply.
      So with 添付する, use 〜に; with 送る, 〜で is common.
What does 添付して mean here? Does the て-form imply “and then”?
The て-form links actions. In this sentence it’s sequential: “attach (the documents) and then send (it).” You could say 添付してから送って to emphasize “after attaching,” but the simple 添付して送って is natural.
Is 送って rude? How does it compare to 送ってください or 送れ?
  • 送って: a plain, direct instruction/request. Fine among peers or from a superior to a subordinate; too casual for business email.
  • 送ってください: polite request; safe for most situations.
  • 送れ: imperative; sounds blunt/commanding. Avoid unless you intend a very strong order.
    Softeners include 送ってね (casual soft), or politer forms like 送っていただけますか / お送りください.
What exactly is being sent by 送って—the documents or the reply?
Grammatically, the explicit object is only for 添付する: 書類を. The object of 送って is omitted and understood from context as “the reply (email/message).” So: “Attach the documents to your reply and send the reply by the deadline.”
Why 期限までに and not 期限まで?
  • までに = “by (no later than).” It sets a deadline by which the action should be completed: 期限までに送って (send by the deadline).
  • まで = “until (up to).” It marks an end point for a continuing state/action: 5時まで待つ (wait until 5).
    For due dates, use までに.
What’s the difference between 返信, 返事, and 回答?
  • 返信 (へんしん): a reply (esp. to an email/message); the act or the reply message.
  • 返事 (へんじ): a reply/response in general (spoken or written).
  • 回答 (かいとう): an answer to a question/survey (content-focused, businesslike).
    In email: “please reply” = ご返信ください; “please answer (these questions)” = ご回答ください.
How do 添付する, 付ける, 添える, and 同封する differ?
  • 添付する: to attach (a file) to an electronic message. Collocation: 添付ファイル.
  • 付ける: to attach/affix in a broad sense (stick, put on). Not the default for email files.
  • 添える: to append/accompany (e.g., 書類に写真を添える). Sounds slightly formal/literary.
  • 同封する: to enclose with postal mail or a physical package.
How do you read the kanji here? Any look-alikes to watch out for?
  • 返信 (へんしん, henshin)
  • 書類 (しょるい, shorui)
  • 添付 (てんぷ, tenpu)
  • 期限 (きげん, kigen)
  • 送って from 送る (おくる, okuru)
    Common traps: 変身 (also へんしん) means “transformation,” not “reply.” 機嫌 (きげん, mood) sounds like 期限 (deadline); different kanji and meaning.
Can I say 返信で or 返信へ instead of 返信に?
  • With 添付する, use 〜に: 返信にファイルを添付する.
  • 返信で works with verbs of sending/informing: 返信でお知らせください, 返信で書類を送って.
  • 返信へ is unnatural here; へ marks direction of motion and isn’t used with 添付する.
How can I rewrite this more politely for business?

Examples:

  • ご返信の際に書類を添付の上、期限までにご送付ください。
  • 書類を添付して、期限までにご返信いただけますと幸いです。
  • More formal/concise: 書類をご添付のうえ、期限までにご返信ください。
Is the comma after 添付して necessary?

No. It’s just a readability pause. Both are fine:

  • 返信に書類を添付して、期限までに送って。
  • 返信に書類を添付して期限までに送って。
Is 書類 singular or plural here? Do I need a counter?

Japanese doesn’t usually mark plural. 書類 can mean “document(s).” If you need to be specific, add a counter:

  • One document: 書類1通 or 書類1部 (context-dependent)
  • A set: 書類一式
  • Two documents: 書類2点/2通/2部 (pick the counter that fits your document type)
Why are there two に’s (返信に, までに)? Are they the same usage?

They’re different:

  • 返信に: target of attachment (“to the reply”).
  • までに: time limit (“by [time]”).
    Same particle shape, different functions.
Can I use 送信する or 送付する instead of 送る?
  • 送信する: technical “to transmit/send” (emails, faxes).
  • 送付する: formal “to send/forward” items/documents (often business).
  • 送る: general “send.”
    Your sentence could be: 期限までに送信して (email context) or 期限までにご送付ください (formal).
Does 返信 refer to the act of replying or the reply message itself?
Both, depending on context. Here, 返信に書類を添付して clearly treats 返信 as the reply message you’re composing and will send.
Would 期限内に work? How is it different from 期限までに?
  • 期限までに: by the deadline (before it hits).
  • 期限内に: within the allowed period (any time before the end).
    In many deadline instructions both are acceptable, but 〜までに is the standard phrasing for “by [due date/time].”
Could I use 締切／締め切り instead of 期限?

Yes. 締切(り) focuses on the cut-off point for submissions; 期限 is a broader “time limit/validity period.”

  • By the deadline: 締切までに送ってください.
  • When validity/expiration matters (e.g., coupons, contracts), 期限 is more natural.