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Level 5

Attaching first 5 times then stops working......

Does anybody else experience this?

  1. You are entering bills / expenses
  2. All has worked for the first 5 times you do this....enter the bill and then attached the PDF receipt
  3. Then the 6th just CANNOT attach the file
  4. You refresh the page.....nope - does not work....
  5. You save the Bill with no attachment and then reopen it to attach the document....does not work 
  6. you try luck


This is so annoying......and happens in Edge, Chrome, Firefox......


QuickBooks Team

Attaching first 5 times then stops working......

Hello Shop Admin, We'd like to take at this and see what could be causing in this case the attachment issue.The document that is not uploading how big is the file? Do you get an error? Is this a file already uploaded in attachments?

Level 5

Attaching first 5 times then stops working......

The error message is that when you save it says that the file has not finished uploading - even after waiting a few minutes.

No the file is not already uploaded and there are no other files in the attachments section

The files are all SMALL pdf files - see example below - all around 130kb size



QuickBooks Team

Attaching first 5 times then stops working......

Let me provide additional information about attachments in QuickBooks, ShopAdmin.


Attachments can't be attached directly to list items, such as Accounts or Employee Names. Attachments can't contain special characters in the file name. Adding an attachment to customer or vendor profiles and their transactions helps organized the records. The security message you received when attaching documents will usually prompt when the file type you're trying to attach is other than the following supported file types. Also, make sure that you're using the accepted characters and file types to avoid any errors.


In addition, take note these are the only file types you can attach in order to protect the security of your account:

  • PDF
  • JPEG
  • PNG
  • DOC
  • XLSX
  • CSV
  • TIFF
  • GIF
  • XML

If the file is already saved as one of the listed supported file types, try removing the extra space between the file and the extension. The file name should look like this "filename.pdf", then add the attachment once more.


If the same issue after checking the requirements of attachments You may be experiencing some browser hiccups. We'll perform the basic troubleshooting to fix this. Let me guide you.


We'll start with logging into your account through a private browser. It's the best place to identify web issues. These are the shortcut keys:

  • Google Chrome: press Ctrl + Shift + N 
  • Mozilla Firefox: press Ctrl + Shift + P
  • Safari: press Command + Shift + N

If you can add the attachment successfully using the private browsing session, go back to your regular browser and clear its cache to refresh the program.


To learn more about how attachments work in QBO through this article: Attachments in QuickBooks Online.


The Community is always open whenever you need help with QuickBooks. Stay safe and have a nice day ahead!

Level 5

Attaching first 5 times then stops working......

Ok, in simple terms - it works approx 5 times then stops working...nothing changes....file names the same format......

It may even be ok for say 20 bills.....then stops working


QuickBooks Team

Attaching first 5 times then stops working......

Hi there, ShopAdmin.


Thank you for coming back to the thread and add further details about your concern in attaching documents in QuickBooks Online. This isn't the kind of feeling that I'd wish you to have, and we know how much time it can take when something isn’t working the way you need it. I'll ensure you'll be routed to the right person to help you ensure that your issue will be resolved.


Since you've done some troubleshooting steps and the issue persists after following the information shared above, I suggest contacting our QuickBooks Support Team. They have the tools to check your account and investigate the cause of why attaching documents stop working.


Here's how to reach them:


  1. Go to the Help (?) icon.
  2. From QB Assistant, enter the topic you need help with. You can also enter questions.
  3. Choose Contact Us to connect with a live support agent.
  4. Choose a way to connect with us.


Please refer to this article to see different information on how adding attachments works in your different transactions: Attachments in QuickBooks Online.


If there's anything else that I can help you with, please let me know in the comments below. Always around got your back here in the Community.

Level 5

Attaching first 5 times then stops working......

ha ha ha ha ha


so you now want me to waste an hour with a support person who know nothing and cannot help


good old SLOWBOOKS.....


I think you should change the name


Level 2

Attaching first 5 times then stops working......

I have had this issue a few times.  Tonight I am doing 10 Expenses and 5 JEs.  Attached to all 15 transactions are the same 2 pdfs.  I attached them all, then went back to enter the data -- had not hit save yet, giving them time to upload - and no they are not huge files.  First 5 expenses with the attachments -- got to 100% but said they were still uploading.  Next 10 uploaded just fine.  That is crazy.  If anything you would have thought the last 5 would be the ones with the hiccup.  But no.  Plus I gave it 30 minutes, still did not upload and let me save.  I then detached the attachments -- STILL won't let me save the transaction, and cannot refresh.  I am going to have to start these stinkin 5 expenses all over again.  The exact SAME attachments, same browser -- GO FIGURE

Level 2

Attaching first 5 times then stops working......

Oh my goodness and now it signed me out of my account.  Grrrrrrrrrrrrrrrr

QuickBooks Team

Attaching first 5 times then stops working......

Hello there, @sandra68588.


If I were in your shoe I would feel the same way of having that error. Let me be your best help.


Let's perform some troubleshooting steps to determine if this is a browser-related issue. Access your QBO account via incognito mode to avoid storing cache files that may cause odd behaviors when running web-based programs. Below are the shortcut keys you can use:


  • Google Chrome: press Ctrl + Shift + N
  • Mozilla Firefox: press Ctrl + Shift + P
  • Microsoft Edge: press Ctrl + Shift + N
  • Safari: press Command + Shift +N

Then, try to put the attachments of the five transactions and save them. If this works, clear the cache of your regular browser to eliminate piled-up data. If the issue persists, you can use another supported browser or device. It might be that the current one you're using has a temporary issue with the program.


After that, if you can't still save your attachments, I recommend reaching QuickBooks Online (QBO) support. They have tools that are equipped to pull up your account in a safe environment and check for possible reasons why it can't be saved. Moreover, they can create an investigation about this if other users are experiencing this issue.


I also have some additional articles about managing a wide range of reports in QBO:



We're grateful to have you here. If you have additional questions, don't hesitate to reply to this post. We'll be happy to help you. Keep safe.

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