Cannot attach word docs to gmail emails

I am trying to attach word 2008 documents to my gmail emails through safari and each time I send it the attachment turns into a strange type of file that is not the original and it loses the integrity of the document. Does anyone know how to fix this? I tried to repair the disk and restart my computer but that didn't fix the issue.

MacBook Pro, OS X Mavericks (10.9.5)

Posted on May 19, 2016 7:56 PM

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2 replies

May 20, 2016 6:29 AM in response to asutton731

If the problem is still there, try booting into the Safe Mode using your normal account. Disconnect all peripherals except those needed for the test. Shut down the computer and then power it back up after waiting 10 seconds. Immediately after hearing the startup chime, hold down the shift key and continue to hold it until the gray Apple icon and a progress bar appear. The boot up is significantly slower than normal. This will reset some caches, forces a directory check, and disables all startup and login items, among other things. When you reboot normally, the initial reboot may be slower than normal. If the system operates normally, there may be 3rd party applications which are causing a problem. Try deleting/disabling the third party applications after a restart by using the application un-installer. For each disable/delete, you will need to restart if you don't do them all at once.

Safe Mode


Safe Mode - Mavericks

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Cannot attach word docs to gmail emails

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