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Sending SMIME messages with sendMail endpoint is broken.

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評估

難度
4/5
預估耗時
3-5 天
新手友好度
35/100
Issue 類型
缺陷
描述清晰度
基本清楚
活躍度
停滯
技術堆疊
java
領域
api

研究方向

從連結的 Microsoft Graph 文件中的 sendMail MIME 範例開始,重現 issue 中所示的 RequestInformation 要求,包括其 Content-Type 和編碼後的本文。將該要求與收到的 multipart/mixed 訊息進行比較,以判斷此行為是屬於 Java SDK 還是 Graph 端點。完成條件是確認 SDK 修正,或記錄 Graph 的限制以及受支援的替代方案。

由索引模型根據 Issue 內容生成。

描述

status:waiting-for-triage type:bug
Describe the bug

Hello,

We are using Microsoft Graph Java SDK to send encrypted SMIME Messages.
We are already encrypting the content and provide a full MIME document to endpoint:
https://graph.microsoft.com/v1.0/me/sendMail

For example our MIME Message looks like this (saved on content variable):

Date: Tue, 10 Feb 2026 11:24:45 +0000 (UTC)
From: [email protected]
To: [email protected]
Message-ID: <....>
Subject: Test2
MIME-Version: 1.0
Content-Type: application/pkcs7-mime; name="smime.p7m"; smime-type=authEnveloped-data
Content-Transfer-Encoding: base64

MIAGCyqGSIb3DQEJEAEXoIAwgAIBADGCAdswggHXAgEAMIGPMHcxCzAJBgNVBAYTAkRFMQwwCgYD
...

We are using the following code snipplet to send the Email:

initializeGraphClient();
String encoded = Base64.getEncoder().encodeToString(content.getBytes());

RequestInformation requestInfo = new RequestInformation();
requestInfo.httpMethod = HttpMethod.POST;
requestInfo.urlTemplate = "{+baseurl}/users/{+email}/sendMail";
requestInfo.pathParameters = new HashMap<>();
requestInfo.pathParameters.put("baseurl", "https://graph.microsoft.com/v1.0");
requestInfo.pathParameters.put("email", config.getMailbox());
requestInfo.headers.put("Content-Type", Set.of("text/plain"));
requestInfo.setContentFromScalar(client.getRequestAdapter(), "text/plain", encoded);

HashMap<String, ParsableFactory< ? extends Parsable>> errorMapping = new HashMap<>();
errorMapping.put("4XX", ODataError::createFromDiscriminatorValue);
errorMapping.put("5XX", ODataError::createFromDiscriminatorValue);

client.getRequestAdapter().sendPrimitive(requestInfo, errorMapping, Void.class);

However our SMIME content is converted into an attachment and send as an attachment packed into a multipart/mixed structure by sending the Email.

Here is what we get on the reciever side:

Content-Type: multipart/mixed;
	boundary="_002_155174533371770722695547_"
MIME-Version: 1.0

--_002_155174533371770722695547_
Content-Type: text/plain; charset="us-ascii"
Content-Transfer-Encoding: quoted-printable

--_002_155174533371770722695547_
Content-Type: application/pkcs7-mime; name="smime.p7m"
Content-Description: smime.p7m
Content-Disposition: attachment; filename="smime.p7m"; size=4483;
	creation-date="Tue, 10 Feb 2026 11:33:38 GMT";
	modification-date="Tue, 10 Feb 2026 11:33:38 GMT"
Content-ID: <[email protected]>
Content-Transfer-Encoding: base64

MIAGCyqGSIb3DQEJEAEXoIAwgAIBADGCAdswggHXAgEAMIGPMHcxCzAJBgNVBAYTAkRFMQwwCgYD

Can you fix sending a SMIME by using this sendMail endpoint or is there any alternative ways for sending SMIME with Graph API?
We basically followed the Example 4 in this documentation page:

https://learn.microsoft.com/en-us/graph/api/user-sendmail?view=graph-rest-1.0&tabs=http#example-4-send-a-new-message-using-mime-format

Expected behavior

Sending SMIME messages should work with the sendMail endpoint when Content-Type is provided as text/plain.

How to reproduce

See the code snipplet above for example code.
We can also provide a full SMIME example content if you want.

SDK Version

No response

Latest version known to work for scenario above?

No response

Known Workarounds

No response

Debug output

No response

Configuration

No response

Other information

No response

主要語言
Java
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