PDFs that are locked will not send in iMessage

Hi,

IF one PDF works and another does not that seems to be too small a sample to say one way or the other.

However generally speaking I would be looking towards a corrupt (even if that is a small corruption) of the PDF file.

Today we pulled out an old Tangerine iBook running Mac OS X 10.3 with only an Ethernet connection and used KidsPix in OS 9

We realised we would not be able to Airprint from there and had not shared the Printer on my OS X 10.12.2 iMac.

We also then found we could not connect to move the file to the G4 (Leopard) for some reason.

The first flash drive we tried was not formatted for that level of the OS.

The second would not store the files (even when converted to .jpg from .pict (QuickDraw) or to a .gif)

Eventually it showed up on the G4 and I was able to transfer it to the iMac without it appearing to be an executable file or saying it was corrupt.

The upshot of that is that it is not ways as straightforward as it seems.

Trying different methods from OX 10.3 to 10.5.8 to OS X 10.12.12 using plain File Transfer and Flash Drives formatted in and for different level of the Mac OS all had issues with an older file type that did not seem to be recognised by Preview when using some methods.

It also appeared that some of the transfer methods corrupted the file when saving/moving it to a particular Flash Drive.

Apple, other than the Hosts who monitor the Post for infringements on the rules, do not monitor these boards.

You can always use http://www.apple.com/feedback or target it down to a specific app or product if it helps.

8:21 pm Sunday; January 15, 2017

Hi,

As your post suggested it may be linked to the Mac OS in some way.

That could be the way the file is being Saved and what happens when you try to share.

The saga I had today with one small picture file was it illustrate that moving such files is not always straightforward.

The other possible is that the process used for file sending in Messages is being blocked by something.

I use and App called Little Snitch that is a Firewall that tells me what App, on what IP and ports, is trying to connect to, either incoming or out going.

This process has nothing in the name to suggest it is Messages of iMessages and so you can end up not allowing and effecting blocking any file sending whether they are pictures or not.

This is the iMessages Login Process.

The File Transfer one has File Transfer in the name (I have not sent any today so I have not allowed the process that only shows up when you first send something).

There is in fact a very similarly named one for AIM and Jabber file transfers.

9:33 pm Sunday; January 15, 2017

Send Apple feedback. They won't answer, but at least will know there is a problem or a suggestion for change. If enough people send feedback, it may get the problem/suggested change solved sooner.

Feedback

It must be a macOS issue. If I upload my encrypted PDF to iCloud and then share it using iMessage form my iPhone, it sends it just fine, and syncs it with macOS as one would expect → I can see the sent file on macOS, and can view it by entering the password.

Apple, you got work to do.

Thank you both. I've already submitted the feedback form.

Ralph, it's not just one file. I do this quite often and only now decided to dig for a solution. I've been circumventing the macOS problem through iOS, as described above, for a while now. Until Apple fixes this, which in my experience will take an age and a half, we will just keep having to do it one of the other ways.

Not sure what your Tangerine tangent has to do with any of this, but thanks for sharing, I guess... (:

HI,

Try Compressing (zip) it in the first place or send in a enclosing folder (which causes the app to Zip it).

There is a sort of known issue that seems to have started with the AIM Servers whereby plain Pic formats are not allowed to be sent.

There have been Malicious Code in some .jpegs in the past and I wouldn't be surprised if other formats now suffer from this.

9:10 p.m. Friday; September 11, 2015

Hi,

I could see that two levels of encryption may possibly cause a conflict.

I can see that possibly a security feature checks a PDF looks like a PDF when it is sent and an Encrypted one looks "wrong".

I have nothing else apart from Compression (zipping) as a way around this.

8:12 pm Sunday; November 22, 2015