Sending SMIME messages with sendMail endpoint is broken.

リンクされた Microsoft Graph ドキュメントの sendMail MIME の例から始め、issue に示されている RequestInformation リクエストを、Content-Type とエンコードされた本文を含めて再現します。リクエストを受信した multipart/mixed メッセージと比較し、その動作が Java SDK に起因するのか Graph エンドポイントに起因するのかを判断します。完了条件は、SDK の修正を確認できること、または Graph の制限とサポートされている代替手段を文書化できることです。

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: HenriettaM@xyz.onmicrosoft.com
To: xxx-test@gmx.de
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: <C06558A1F17AA04CAE95309F8C325E89@namprd19.prod.outlook.com>
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