Customers are NOT able to open all of my pdf attachments.

Question

I have recently began having consistent issues with people being able to open my attachments within my emails. These are not usually extremely large files either. They are able to open one file, but not another. I was saving all of my files on a thumb drive, but was told that it may be corrupt, so I started to save all of my files (invoices from Zoho) and my pdf paperwork files to OneDrive. They are able to receive all of my files now only sometimes, but not most of the time anymore.

I have also started to send the emails from my yahoo, that I need to send to my customer, to myself with my alternate gmail email account. At least this way I know if they are going to be able to open them. Some files upload, and the ones that wont open, give me a notice saying: Could not preview the file. You may be offline or with limited connectivity. OR the file will not even open or even show up in their email at all. Then if I try to resend it from my gmail account they will all show up. There is no consistency all of a sudden. I ran an internet speed test and its pinging at 16 MS / Download: 561.75 Mb/s / Upload: 22.52 Mb/s. I have also recently cleared all of my cache on my computer as well.

Today, I did notice that my Microsoft 365 has expired on my Windows 10 operating system, but I cant find where to remedy that. I did click on my update software toady. I have no clue what is going on and am constantly wasting time trying to guess as to what could possibly be wrong with my customers NOT being able to open my files that are saved in OneDrive. Any assistance would be greatly appreciated. Thank you so much!

Answer 1

Hello Lesha Stephens,

I’m sorry this has been so frustrating. Since the same PDFs send successfully from Gmail, the issue is more likely with Yahoo’s attachment upload/preview process than OneDrive or the internet connection; an expired Microsoft 365 subscription would not normally explain why Yahoo omits only certain attachments.

Please try the options below and check whether the issue continues:

1. Open each PDF directly from the OneDrive folder first. If it opens normally, download or copy it to the Desktop, then attach that local copy to a new Yahoo email. Wait until the attachment finishes uploading before selecting Send.
2. Rename the file using a short, simple name such as Invoice123.pdf, avoiding symbols such as #, %, &, or very long names.
3. Try Yahoo Mail in a private/incognito window or another updated browser, with browser extensions temporarily disabled. Clearing the cache alone may not rule out an extension or Yahoo session issue.
4. If attaching still fails, send a OneDrive sharing link instead, after checking that the recipient has permission to open it. As a temporary workaround, continue using Gmail for urgent invoices.
5. Renew Microsoft 365 separately at https://account.microsoft.com/services. Confirm that the account shown there is the same one used for the subscription.

Please let me know how it goes after trying these steps, and I'll be glad to continue looking into it with you.

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