Upright_Artistic

macrumors newbie
Original poster
Nov 12, 2019
2
0
I'm completely new to Mac. I'm having an issue, when I try to send a photo that's located on a external drive I get the following "not delivered" message pictured below. But when I move the photo from my external drive to the desktop the photo will send no without any issue. Is there a reason Mac behaves this way? Why can I not send a photo on an external drive? Thanks for the help.
 

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Brian33

macrumors 65816
Apr 30, 2008
1,011
135
USA (Virginia)
I can't think of any reason it should behave the way you described! Weird. You should be able to send photos located an external drive.

Oddly, your image attached does not show a "not delivered" message -- it shows two photos.

Are you still having trouble?
 
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Upright_Artistic

macrumors newbie
Original poster
Nov 12, 2019
2
0
Oddly, your image attached does not show a "not delivered" message -- it shows two photos.

Are you still having trouble?

Thanks for the reply...I’m still having trouble.

In the lower right hand corner of the screen capture there’s a red indicator that says “not delivered”
 
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Brian33

macrumors 65816
Apr 30, 2008
1,011
135
USA (Virginia)
Oh -- I missed the "not delivered" indication, sorry.

Huh. It looks like you're sending via Messages. I played around with sending a photo with Messages from an external hard disk drive but didn't notice anything odd...

Your external drive is probably slower than your internal drive, but it shouldn't make any significant difference. I'm assuming you're not disconnecting or ejecting the external drive before the photo is completely sent (which can take awhile). I'm also assuming the photo on the external drive is just a file you're accessing with Finder. Or, is it in a Photos.app library, or some sort of archive (like a .zip file)? Does this problem seem to happen for any photo on the external drive, or just a particular photo?

Might be worthwhile to copy the photo(s) to a different external device (a HDD or a USB flash drive, for example) and see if you have the same behavior -- to determine whether the issue is specific to a particular device.

So far I'm at a loss to explain why you're seeing this issue! Very odd, and it must be frustrating.
 
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astonius86

macrumors member
Apr 25, 2017
90
24
Mt Juliet, TN
Wow, I was searching for this issue and found this thread. My drive isn't external, but it's a different internal drive than the main system drive. I copied the photo from the second drive to the main drive, and sure enough it sent without issue. So weird, and very frustrating. I'm running 10.15.1. The secondary drive is formatted in exFAT.
 
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whyunowork

macrumors newbie
Nov 23, 2019
1
1
Wow, I was searching for this issue and found this thread. My drive isn't external, but it's a different internal drive than the main system drive. I copied the photo from the second drive to the main drive, and sure enough it sent without issue. So weird, and very frustrating. I'm running 10.15.1. The secondary drive is formatted in exFAT.

double wow I JUST now started to experience this issue after updating from Mojave to Catalina 10.15.1

I was only able to send photos/documents once I put them onto my desktop
 
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Mark Den Hartog

macrumors newbie
Feb 9, 2020
3
2
I am seeing the exact same thing. updated to Catalina yesterday and I can only send from my internal drive.
My iMac starts spinning the fans like mad as well!??
Just changed permissions to "everyone" ,problem persists.
 
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Brian33

macrumors 65816
Apr 30, 2008
1,011
135
USA (Virginia)
I think I saw somewhere that this was a bug that might be fixed in one of the Catalina updates. Have you applied all the updates? Not sure but I think Catalina is up to 10.15.3 now.
 
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mikzn

macrumors 68030
Sep 2, 2013
2,627
1,879
North Vancouver
Just tried it on Catalina 10.15.4 - it works but but is very slow - took a few minutes to send a 215k picture from an external HDD drive - it's like "go have a coffee" slow

Edit - maybe I spoke too soon - tried it again with a larger picture and it stalled out at around 95%
 
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Mark Den Hartog

macrumors newbie
Feb 9, 2020
3
2
Yep. still busted. 10.15.3 here. Calling apple tomorrow if I have time.
[automerge]1581280308[/automerge]
I think I saw somewhere that this was a bug that might be fixed in one of the Catalina updates. Have you applied all the updates? Not sure but I think Catalina is up to 10.15.3 now.
Thanks Brian! I am on the latest version.
 
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_Alex_

macrumors newbie
Feb 10, 2020
1
0
Hit this thread, because I was searching Google for solution. Same crappy issue here after upgraded to Catalina. The issue still persist even after all OS updates are applied. I have a Lacie external SSD connected to one of the TB3 ports and I can access all the files and folders w/out any issue. However, when I try to send a photo, which is located on the external drive via iMessage, it just takes few minutes to "try" and then it gives up without sending it. When I copy the photo anywhere on the local SSD and send it via iMessage it is OK.
It is obviously a dumb bug. Apple has to fix this crap.
 
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adenbeckitt

macrumors member
Jun 23, 2010
75
0
Just updated to Catalina today as I was sure all the bugs must have been squashed by now... I was wrong. This is a deal breaker for me, I send so many files like this. Annoyed is an understatement.
 
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xtol121

macrumors newbie
Mar 26, 2020
10
9
I'm experiencing this as well. I have my primary drive partitioned and I can not use Messages to send a picture from the new partition.
 
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nursegal53

macrumors newbie
May 19, 2020
2
0
I am very frustrated. I cannot send photos on iMessage. Thought my old MacBook Pro was just needing to be replaced and got a new Air yesterday. All excited that I would be able to send photos and I am having the very same problem with this computer. I chatted online with an Apple support person last night and got nowhere. He couldn't figure it out although I can't believe they are not hearing about this issue. Also on Catalina 10.15.4. I have already been all over the web looking for answers to this problem and not getting it solved.
 
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Taz Mangus

macrumors 603
Mar 10, 2011
5,438
1,598
I just tried 3 different tests to send a picture from messages. First one from an external hard drive, second one from a second partition on the internal drive, and last one from the main partition on the internal drive. All failed as Not Delivered. I did some searching and someone mentioned to copy the picture within Messages and send that. I tried that it did work on the 2 instances that I tried. The interesting thing is that sending the copied picture within Messages app was a lot quicker at sending then even attempting to send the picture from the main partition on the internal drive.

I even tried logging out of Messages app, rebooting to safe mode, rebooting back to normal mode and logging back into Messages app without any success as sending a picture.
 
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nursegal53

macrumors newbie
May 19, 2020
2
0
My son has been helping me to try to figure out a fix. He just reset my MB Pro back to Maverick from the newest Catalina update and iMessage sends photos just fine now. Definitely something to do with that operating system. But he also has a MB Pro with Catalina on it and it works fine. So the question for me now is, what do I do with my new MB Air that isn’t working? This just shouldn’t be a problem on a brand new computer.
 
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brandonjoseph

macrumors newbie
May 30, 2013
2
0
Just found this thread after googling this problem. Before I elaborate I will give some background

-Brand new Mac Mini I purchased 1 week ago with 2TB internal SSD
-Brand New G-Technology (Western Digital) 4TB HHD, formatted for Mac (journaled)

Some images would not send in Messages, others would. After testing I discovered it was only images from my external HDD.

Just got off the phone with Apple, escalated to a third tier of specialist, I think. Apparently they are aware of this "issue" (didn't call it a bug). He had me send some log files to Apple, and although he said he would call me back in about a week, he did admit that this process was mostly for reporting reasons and not to try and fix my particular case. I'm annoyed but also somewhat relieved that it is a known issue and not something wrong with my appleid/icloud setup. For now I'll just be copying to my desktop 🤷🏼‍♂️

tl;dr:
happens only when sending from external HDD. Called apple. They're aware of issue. No fix currently.
 
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durancd

macrumors newbie
Jun 5, 2020
1
0
This has been a bug for months now and apple is aware of it. My recommendation would be to go to the Apple Feedback page for macOS and iMessage, submit this as a bug report like I have, and perhaps it will get some attention. It is affecting a large number of people but I believe they ignore the forum discussions and only pay attention to feedback submissions.

It’s pretty sad because many people who don’t use their boot drive for Image storage can’t easily drag drop image files to send any more without first copying to the boot drive… a terrible work around.
 
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UA: Class 1-C

macrumors newbie
Jun 7, 2020
1
0
Kame House island
I'm completely new to Mac. I'm having an issue, when I try to send a photo that's located on a external drive I get the following "not delivered" message pictured below. But when I move the photo from my external drive to the desktop the photo will send no without any issue. Is there a reason Mac behaves this way? Why can I not send a photo on an external drive? Thanks for the help.
so for a while I was just thinking my iMessage couldn't send large files, but thats because everything I was trying to send was coming form my hard drive. im a photographer and id send photos from there.... I literally after 7 months realized that it would send from my computer. before I was screenshooting and sending... I should of noticed then. OLDER IMACS don't have this issue, so the people responding without having issues might have older models
 
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