Hi Brian,
1. Are you trying to send the statement using Mail app using
the webmail?
2. Which account are you using to send the statement?
3. Is the issue confined to sending QuickBooks statements?
4. Which version of QuickBooks are you using?
5. What steps did you try to fix the issue?
This issue seems to be related to
QuickBooks PDF Converter Activation Error and also related to QuickBooks compatibility with Windows 8.
For further information, refer to the article:
Unable to reconcile accounts or
to create, print, or email .pdf files
Note: Only
QuickBooks 2013 R4 and later is supported on Windows 8. Do you use Windows 8 64-bit and QuickBooks 2011 or 2012? They weren't designed for Windows 8 so this article won't help.
If the Quickbooks version you are using is not compatible with Windows 8, you may try running Quickbooks in compatibility mode and check.
For further information, refer to the article:
Make older programs compatible with this version of Windows
You may also get in touch with
QuickBooks support to check for the issue.
QuickBooks Knowledge Base
Hope the information helps. Let us know if you need further assistance with Windows related issues. We will be happy to help.