Must send .PDF via Message from iPad using iPadOS 17.4.1

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Level 1

17 points

Must send .PDF via Message from iPad using iPadOS 17.4.1

I have .PDF document with mandatory guidelines which requires it be sent via messaging. I had been sending this document this way for years because 1) the Receiver requires it; and 2) because they don’t use email.

I did convert the document to .PDF from Pages, saved it to my ipad and tried sending by choosing Acrobat>Browse files>On My ipad>document.PDF, then clicking send, which quickly and continuously returned a “Not Delivered” Red error message.
Then I tried converting the document to image in Pages and it went out successfully, BUT the .jpeg format was unacceptable and incorrect according to the mandatory guidelines of the Receiver.
So then, I attempted the same steps I did to send the image; except sending .PDF from in Pages and again, it retuned the “Not Delivered” Red error message.
I opened the .PDF in Acrobat and attempted sending it only to receive the “Not Delivered” error message.

PLEASE HELP! I welcome any and all suggestions as to how I can send this .PDF using Apple Messages? I have an absolutely critical deadline to send this document out via of Messenges.

iPad Air, iPadOS 17

Posted on Apr 5, 2024 2:29 PM

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Answer 1

cgaylord5784 Author

Level 1

17 points

Apr 5, 2024 9:59 PM in response to Alancito

Alancito, thank you so very much for your quick response and insight. It has been helpful in that you gave me a quick lesson on house to create a short cut. I had never open the Shortcut app but I literally have 100s of them, maybe because I have Siri doing things while I’m driving (pst…auto insurance and cell phones). Who knows, but I finally opened the .pdf in Acrobat Reader and allowed it to go into Acrobat cloud. Then I went to Messages, chose Acrobat and the file was sent, then went back to the cloud and deleted it. I don’t trust Adobe with my files since they were breached. So I will still be looking for a way to send it directly without having to use Acrobat Cloud. I have to this time next month to find it.

in the mean time I will hear tomorrow morning if it is accepted via Acrobat.

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Answer 2

6x6

Level 6

19,599 points

Apr 5, 2024 5:02 PM in response to cgaylord5784

This could be due to your MMS settings. On your iPad (if you have the cellular model) or on your iPhone (if you've set the SMS transfer), go to Settings > Messages and make sure MMS Messaging is activated.

If it already is, turn if off, restart the device (iPad cellular or iPhone) and turn it on again.

If the problem persists, please contact your carrier as there could be an issue on their side.

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Answer 3

Alancito

Level 7

30,156 points

Apr 5, 2024 2:54 PM in response to cgaylord5784

cgaylord5784 wrote: "...I welcome any and all suggestions as to how I can send this .PDF using Apple Messages?..."

cgaylord ~ Apple's Shortcuts app has a Send Message action — so try a simple custom shortcut:

Shortcuts User Guide - Apple Support

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Answer 4

cgaylord5784 Author

Level 1

17 points

Apr 5, 2024 9:41 PM in response to 6x6

6x6 my settings for Massages does have SMS enabled. It has been for years. I follow Alancito suggestion to create a Shortcut, which works fine on my end but still gives the “Not Delivered” error message. I can send an image with no problem. Messages will ONLY allow a .pdf attachments from the Acrobat cloud folder. My problem with that is Adobe has been breached before, so I don’t trust it with confidential files.

i thank both you and Alancito for your insight and help.

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Answer 5

cgaylord5784 Author

Level 1

17 points

Apr 6, 2024 2:59 PM in response to 6x6

I know, both SMS and MMS are enabled. Apple’s OS update only allows .PDFs to be send from Messages via Acrobat Cloud. I have tried everything, and it’s the only thing that works.The Director called me this morning and said they will let me know Tuesday if the document can be accepted being delivered via a Third-Party App. The way they have it setup the file is encrypted coming directly from my device. Right now it’s more technical than I am allowed to explain, but basically it’s routed from my phone via Adobe Cloud to them, which breaks the encryption. So if it is not acceptable, I guess I will be taking a flight to Corporate to deliver a document. I think it’s issues like this that have Congress’ panties in a bunch about Apple. Even before this issue, I have had problem before OS 17 with formatting and pictures when I send it and losing it’s format when it’s open on an Windows or Linux desktop or an android device and that also was with SMS/MMS enabled.

Anyway, I’ve said too much. Thank you again for your insight, it is greatly appreciated.

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