Problem with sending attachments

Question

I have a problem with sending attachments to some specific recipients.

Recipients receive body of my mail, but attachments are missing.

Only I have this problem in my company.

I tried Insert-Attach File, I tried Drag and Drop option, I tried to send mail from Outlook Web App...didn't help.

Answer 1

HI Nikola,

Sorry for the delayed reply.

Based on the message header you sent via private message, the parameter “X-MS-Has-Attach” of these two message headers are shows as below which means the attachment are sent out successfully.  

X-MS-Has-Attach	yes

To do further troubleshooting, please help us confirm:

1. The msg files of these two emails: an email withno attachments from the external recipient’s side the other one is an email withattachments from the external recipient’s side (sending by the sender’s smart phone).  You can refer to the following steps to save the msg files (Please upload the msg file to the workspace via private message).
2. Opens the email in the Outlook client> file > Save as > Save as type: Outlook Message Format – Unicode.
3. Could you please provide the screenshots of the message trace result on the problematic sender (one with attachments sent successfully via phone and another with no attachments) in the Exchange Admin Center of your Organization?
4. About “when sender (our employee) send mail via Outlook (same account) from her smart phone (Android), recipient receive attachments”, please check if the user can send out emails with attachments to the same external recipients via Outlook Web App.

For privacy concerns, I have sent you a private message to collect the information, please click on the link below to access your private message.

https://answers.microsoft.com/en-us/privatemessages/list

Thanks,

Poppy

Answer 2

Hi Nindzara,

To narrow down the issue, please try the following:

1. Check if the problematic users can receive the attachments via Outlook Web App (OWA: https://outlook.office365.com/owa).
2. Press “Ctrl” key and click the Outlook icon to open Outlook in safe mode, then check if the problematic users can receive attachments.
3. Note: if the users can receive the attachments in safe mode, the issue might be related to add-ins.
4. Let the problematic users create a new Outlook profile.

Meanwhile, I’d like to collect more details to better understand the situation:

1. Can you send emails to other users with attachments successfully? You can create a test blank word file and send it to yourself and the specific users via OWA and check the result. This can help us determine if the issue is related to your side or the receivers' side.
2. What is the kind of the specific recipients, external or internal?
3. Involve the administrators of your organization to check if there is any transport rules to stop the specific users from receiving attachments.
4. Can the specific users receive attachments from any other users?

Thanks,

Gary

Answer 3

Gary,

1. Yes I can.
2. Recipients are external.
3. I'm administrator. Actually, I don't have that problem, one of our employees has. I tried to re-create profile, I tried to re-install Office2016.
4. Yes, they can. When our employe try to send mail with attachment,  via outlook via OWA, to problematic recipients, results are nagative. Than I send via my outlook, and they recieve attach.

Answer 4

Hi Nindzara,

Thanks for your updates.

From the reply, let me clarify the situation:

1. The problematic recipients are external.
2. The senders can’t send the emails to the recipients with attachments via Outlook or Outlook Web App.
3. You (administrator) can send the emails with attachments to the problematic recipients successfully.

To determine if the issue is related to the senders in your organization or the receivers, please provide the following information:

Run a message trace on the senders (send emails to the problematic users) in your organization and provide the screenshots of the results. To run the message trace, please refer to the article below:

https://technet.microsoft.com/en-sg/library/jj200712(v=exchg.150).aspx

1. Check if the senders can send emails with attachments successfully to other external recipients, like Gmail, Outlook.com, and Yahoo.
2. Can the problematic receivers receive emails with any type of attachments, like Word, Excel or PDF from the senders in your organization? Or just some attachments with special files name extension (like .rar, .dll and .exe) or the larger size attachments can’t be received by the receivers.
3. Does the receivers also use Office 365 Exchange Online service?

Thanks,

Gary

Answer 5

Hi Gary,

1. Yes thay can.
2. Yes, I tried to send .exe, .docx, .pdf

I sent to my private yahoo and gmail accounts

3. No, they are not.

Thanks,

Nikola