Winmail.dat received ONLY when an invoice is sent in bulk

Thanks for reaching out to the Community, RJ4242.
 

When an email recipient receives an attachment called Winmail.dat instead of a .pdf file for their invoice, this is a known issue for Microsoft outlook if the recipient's email client isn't capable of receiving rich text format.
 

If only one or some customers are experiencing this, it can be due to a problem on the receiving end. Certain security and mail filters may detect these emails as mass emailing. This can be fixed by adjusting your message format accordingly in Outlook. Be sure to choose HTML or plain text to prevent Outlook from attaching a Winmail.dat file when sending the email. You can find detailed steps for changing these settings on Microsoft's website.
 

Your other option is to use an email service other than Outlook when sending emails from QuickBooks.
 

Please don't hesitate to send a reply if there's any additional questions. Have a lovely day!

Hi Zach and thanks for the reply.  I have already adjusted Outlook to send as Plain Text.  I did that a couple of weeks ago, I just had to wait until yesterday when the bulk invoices went out.  As I said in the OP, we couldn't test this until now because sending a single invoice to this customer is received properly.  That seems to indicate that the Outlook settings are fine.

I will check into the spam filter at the customer location (thankfully we're an IT services provider, so we can check our client's settings pretty easily).  If I find anything there, I'll update.

Hi, just wondering if you have had any luck with this issue? I have been dealing with this exact issue since we upgraded to Premier Plus 2022 in May with no solution, other than to use a different email provider, which is not an option for my corporate organization and probably isn't feasible for most businesses that are using Quickbooks. 

We have the same problem with one user in our office. Her QB invoices go to customers as a win.dat file.

Mine go out as a regular pdf file. Our QB and Outlook settings are identical. If she sends a file to a customer who receives it as win.dat, and then I send it, they get a pdf from me. This would clearly indicate that it is a Quickbooks problem and not an Outlook problem as we are being told.

We shouldn't have to do 'work arounds' for a program we pay in excess of 2.5K a year for. And it's a problem that is persisting from 2021 into the 2022 version. Intuit, when will this get fixed?

Hello, clutterbug. 

I've checked with my resources and have not found any similar issue with yours. 

In this scenario, since the issue persists, I suggest contacting our Customer Support team. One of our agents will be able to pull up your account and check the issue you encountered.  

Here's how: 

1. Open QuickBooks.
2. Go to Help, then select QuickBooks Desktop Help.
3. Select Contact Us.
4. Give a brief description of your issue, then select Let's talk, and then choose a way to connect.

Visit our QuickBooks Help Articles page for more insight s about managing your business in your software.

I'd like to know how you get on after contacting our support as I want to ensure this is resolved for you. Just reply to this post, and I'll get back to you, Take care always. 

Thank you for your kind reply. I have done as you suggested. I was told it was a known problem and I would just have to wait for an update that fixed it. That was months ago. It's not fixed. And you can imagine my frustration as a business owner, as the person who does the bulk of the billing has the issue with winmail.dat

Constant requests to resend it. We've invented our own work around, but when I pay in excess of $2.5K for software, I expect it to work and when it doesn't, I expect it to be fixed. Searching on the QB support site, I see I'm not the only company with this issue.

I 2nd everything mentioned below. I have talked with Customer Support as well and the help offered is not an option. The only thing they could suggest was using a different email provider (we use Microsoft Outlook). I'm sure you can understand, in the business world, changing email providers is not an easy fix as your suggestion makes it seem. When you have hundreds of invoices to send, its quite frustrating, not to mention time consuming, to go through and individually send invoices to clients to avoid the embarrassment when a client gets an odd looking email that sometimes gets mistaken for spam.  

I've read several other threads about this same issue, I don't believe we are the only 2 clients experiencing this.  

I can see the importance of being able to receive emails in a correct format, christinarodriguez23.

You can let our product team know how this feature is useful for your business needs by sending feedback. To do this, you can follow the steps below:

1. Click the Help menu.
2. Select Send Feedback Online.
3. Choose Product Suggestion and click Send Feedback.
   
   

Additionally, learn how to create email templates with customized subject lines and email bodies when sending sales forms or other transactions. I've got this article for your guide: Create Custom Email Templated In QuickBooks Desktop.

Reach out to us if you have any concerns when sending email. Again, we're always right here to help you.

I'm not sure you are understanding what Christina and I are trying to say. This is not a product suggestion.

This is a software bug in QB. It needs fixing!

I have brand new, windows 11 computers. This problem is pervasive. And on our computer it doesn't matter if its sent out individually or in bulk. ALL OF A SUDDEN QB goes from sending emails as pdf's to winmail.dat format.

Its a bug not a product suggestion for a useful feature. 😁

It isn't the kind of experience we want you to come across, 

At this time, I'd recommend reaching out to our Phone Support team. One of our agents there can expedite what causes the issue. They can also create an investigation into this matter.

You can contact them through the Help menu.

Also, feel free to visit our Help Articles page for more resources about managing your business.

Don't hesitate to get back to this thread if you have questions.

Were you ever able to resolve this issue? I am hoping upgrading to QuickBooks Desktop Enterprise 2024 would fix it but probably not...

Upgrading to a newer version of QuickBooks Desktop (QBDT) and installing its latest release ensures the program is running with the newest fixes and patches, sjstange. Since it isn't doing so, we encourage you to contact the next available support to further investigate this matter.

To do this, here's how:

1. Open QuickBooks.
2. Go to Help, then select QuickBooks Desktop Help/Contact Us.
3. Select Contact Us.
4. Give a brief description of your issue, then select Continue.
5. Sign in to your Intuit account, select Continue, and then Continue with my account.
6. We'll email you a single-use code. Enter your code and select Continue. If you have more than one account, select the account you want to use and then Continue.
7. Select to chat with us or Have us call you.

Moreover, if you wish to learn what to do when Winmail.dat file is received instead of a .pdf file when sending an email through Outlook from QBDT, please see this article: Winmail.dat is attached instead of a .pdf file when sent from QuickBooks through Outlook.

Additionally, you can customize email templates and use them to send messages from QuickBooks. For a complete guide on how to do this, you can check out this article: Create custom email templates in QuickBooks Desktop.

Please feel free to get back to this thread if you have other concerns about sending emails through Outlook from QBDT. We in the Community are always ready to help you out.