Why can't I send Pages files on Gmail?

When I upgraded to Mavericks and the latest Pages, I lost the ability to send Pages files through Gmail. It tells me that the file type is not supported. This happens even if I change the extension to .docx, and even if I use the Gmail webapp. Does anybody know how to fix this? Is there a new setting in Mavericks that I'm missing?

Pages '13-OTHER, OS X Mavericks (10.9)

Posted on Nov 4, 2013 5:26 PM

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16 replies

Nov 16, 2013 8:11 AM in response to Iloveapple314

This is caused by the Google content-filter not recognising the new (Mavericks specific) Pages file-format. Until Google alter there screening process all Mavericks based Pages documents will be blocked as "malicious content".


The work around (in Pages) is to export the document as Pages 2009. This can be attached to an email and sent via Gmail. Note by the way that Mac users who have not upgraded to Mavericks may also be unable to read your Mavericks specific Pages files.

Nov 16, 2013 8:46 AM in response to Iloveapple314

As has already been mentioned, gmail doesn't recognize the new pages file format as a vlaid Pages document and considers it malicious content. This will eventually be worked out. In the meantime as Keith McFarlane suggests you can export the page as Pages 2009. It works but its ugly. You can also archive it it. (Select the file with a right click and select compress.)

Nov 19, 2013 2:02 AM in response to Iloveapple314

Same Problem here


IWORKS 09 pages, keynote, numbers does not send in MAIL (mac) because of "This message was blocked because its content presents a potentialsecurity issue"


its a problem not only on GMAIL but also Live, Hotmail, Yahoo, and other services...


The problem is that gmail and others haved yet accepted the latest iworks 09 files. its a problem that apple can ask then to fix but its up to the gmail and others to fix it.


Solution!!!:


1 - Send it by exporting to office files

2 - Saving the files as old iwork documents

3 - Command P and save as PDF

4 - Save in icloud and send the URL


So you can still send them 🙂 but have to take a bit more of your time 😟



i hope you understand my english is not optimal 😝


And if you have any questions feel free to ask me

Jan 9, 2014 7:41 AM in response to Iloveapple314

So this problem dates back to around October, from what I can see. How is it possible that 3 months later, it hasn't been fixed? I understand companies competing with each other/not being friendly, but doesn't everyone just want to make their customers happy? There seem to be a lot of unhappy gmail/apple customers right now, and I don't understand why no one is responding to this.

Jan 9, 2014 8:06 AM in response to cmatchell

Don't want to come to anybody's defence, but I think is non-trivial to fix for either Apple or Google.


Apple obviously decided to change a file format, using unpacked directories instead of zipped ones. (I personally believe that this is a bad decision.) So fixing this is not a fix but an architectural change.


For Gmail this is also non-trivial, because "fixing" this would, mean to transparently pack and upack directory structures when the user attaches a directory to an e-mail or saves it to their desktop. For a desktop mail user agent (like Thunderbird or Outlook) that's certainly possible technically (although likely problematic from an interoperability perspective), but for a web-based e-mail client like Gmail it might be hard if not impossible.

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Why can't I send Pages files on Gmail?

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