Recipients are unable to open my attachments.

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Level 1

0 points

Recipients are unable to open my attachments.

Hi all,

First time posting so please excuse any misused terminology and the like. I'm having trouble with Mac Mail. I use iCloud mail for my service and I have my iCloud account connected to "Mail" on my iMac. I also have a Hotmail account connected to Mail that I occasionally use.

I recently tried to send a PDF to a Windows user using my iCloud account but they were unable to open the attachment. They could view the message fine and the attachment showed up but they were getting an error when they tried to open it. They also tried to save the attachment to their computer and then open it with no luck. When I took a look at the sent e-mail I was also unable to open the PDF. I was getting an error that read:

"Adobe Reader could not open 'Order Receipt.pdf' because it is either not a supported file type or because the file has been damaged (for example, it was sent as an e-mail attachment and wasn't correctly decoded)."

So I tried again with another file type, this time it was a tiff image with similar issues. Still unable to open the file getting a different error message. I then tried using my Hotmail address as the sending e-mail account, still with no luck. I then was forced to use the Hotmail web site to send the mail and that worked fine, much to my chagrin. I then tried to send it via the web based version of iCloud which didn't seem to work from my end at first, I was unable to open the file by clicking on it, still receiving the same error message mentioned above but when I saved it to my downloads folder I was able to open it up clicking on the file from my downloads stack on the dock. Once it opened up this way I was also able to open it up by clicking on the file in the e-mail.

Upon further investigation, I noticed I was unable to open any attachments to an e-mail as soon as I attached them. When I attach a file by clicking and dragging the file into the e-mail, the icon shows up in the mail, which is strange because normally the attachments show up embedded in the e-mail, but when I click on them I get the error message and the file size for the attachment is 0KB. If I try to attach something using the paperclip icon at the top of the mail message a window opens up where I can select the file but when I select it and click "Choose File" the file selection window closes but nothing seems to have attached to the e-mail.

I've been researching this for a few days now and I've tried rebuilding my mailbox, to no avail.

Sorry if this is a little wordy but from what I've seen in forums, the more information you give on what you've done, the better.

Any clue what's going on?

Thanks in advance!

iMac, OS X Mountain Lion (10.8.4), Mid 2011 iMac, Mail version 6.5

Posted on Jul 19, 2013 12:39 AM

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Answer 1

TehPwN

Level 1

10 points

Jul 19, 2013 2:51 PM in response to kijiro.92mac

I've seen this countless times; all you need to do is have the recipient double click on the attachment in order to view it

Edit: spelling

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Answer 2

Jul 19, 2013 2:53 PM in response to kijiro.92mac

Where are you getting the attachments from? Have you tried something form another source, most likey its the way the images are formatted or sourced from.

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Answer 3

kijiro.92mac Author

Level 1

0 points

Jul 19, 2013 6:49 PM in response to TehPwN

Double clicking wasn't the answer. I've tried that with the same results.

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Answer 4

kijiro.92mac Author

Level 1

0 points

Jul 19, 2013 6:54 PM in response to I Nefarious I

Nefarious, the attachments were coming from my desktop. Upon reading your post I wondered if that was the problem. It appears it is. I've since tried to attach files from my downloads folder with success but found out that files I try to attach from most of my other folders don't work. I've not tested all of my other folders but for now the only one I've had success with is my Downloads folder.

The plot thickens.

I'm trying to think what events coincided with this problem and the only thing I can think of off the top of my head is that around the same time this was going wrong I created another user account on my Mac for my wife. I don't think that is what is causing this but I don't know as much about the inner workings of OSX as most of the people on this forum.

Thanks for taking the time to post guys. Anyone else have any ideas?

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Answer 5

Linc Davis

Level 10

209,547 points

Jul 19, 2013 8:09 PM in response to kijiro.92mac

Please follow these directions to delete the Mail "sandbox" folder.

Back up all data.

Triple-click the line below to select it:

~/Library/Containers/com.apple.mail

Right-click or control-click the highlighted line and select

Services ▹ Reveal

from the contextual menu.* A Finder window should open with a folder named "com.apple.mail" selected. If it does, move the selected folder — not just its contents — to the Desktop. Leave the Finder window open for now.

Quit and relaunch Mail, and test. If the problem is resolved, you may have to recreate some of your Mail settings. You can then delete the folder you moved and close the Finder window. If you still have the problem, quit Mail again and put the folder back where it was, overwriting the one that may have been created in its place. Post your results.

Caution: If you change any of the contents of the sandbox, but leave the folder itself in place, Mail may crash or not launch at all. Deleting the whole sandbox will cause it to be rebuilt automatically.

*If you don't see the contextual menu item, copy the selected text to the Clipboard (command-C). In the Finder, select

Go ▹ Go to Folder...

from the menu bar, paste into the box that opens (command-V). You won't see what you pasted because a line break is included. Press return.

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Answer 6

kijiro.92mac Author

Level 1

0 points

Jul 19, 2013 11:45 PM in response to Linc Davis

Ok, I tried that but i'm still experiencing the same problem as before.

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Answer 7

Linc Davis

Level 10

209,547 points

Jul 20, 2013 9:21 AM in response to kijiro.92mac

Please read this whole message before doing anything.

This procedure is a diagnostic test. It won’t solve your problem. Don’t be disappointed when you find that nothing has changed after you complete it.

Third-party system modifications are a common cause of usability problems. By a “system modification,” I mean software that affects the operation of other software — potentially for the worse. The following procedure will help identify which such modifications you've installed. Don’t be alarmed by the complexity of these instructions — they’re easy to carry out and won’t change anything on your Mac.

These steps are to be taken while booted in “normal” mode, not in safe mode. If you’re now running in safe mode, reboot as usual before continuing.

Below are instructions to enter some UNIX shell commands. The commands are harmless, but they must be entered exactly as given in order to work. If you have doubts about the safety of the procedure suggested here, search this site for other discussions in which it’s been followed without any report of ill effects.

Some of the commands will line-wrap or scroll in your browser, but each one is really just a single line, all of which must be selected. You can accomplish this easily by triple-clicking anywhere in the line. The whole line will highlight, and you can then copy it. The headings “Step 1” and so on are not part of the commands.

Note: If you have more than one user account, Step 2 must be taken as an administrator. Ordinarily that would be the user created automatically when you booted the system for the first time. The other steps should be taken as the user who has the problem, if different. Most personal Macs have only one user, and in that case this paragraph doesn’t apply.

Launch the Terminal application in any of the following ways:

☞ Enter the first few letters of its name into a Spotlight search. Select it in the results (it should be at the top.)

☞ In the Finder, select Go ▹ Utilities from the menu bar, or press the key combination shift-command-U. The application is in the folder that opens.

☞ Open LaunchPad. Click Utilities, then Terminal in the icon grid.

When you launch Terminal, a text window will open with a line already in it, ending either in a dollar sign (“$”) or a percent sign (“%”). If you get the percent sign, enter “sh” and press return. You should then get a new line ending in a dollar sign.

Step 1

Triple-click the line of text below on this page to select it:

kextstat -kl | awk '!/com\.apple/{printf "%s %s\n", $6, $7}' | open -f -a TextEdit

Copy the selected text to the Clipboard by pressing the key combination command-C. Then click anywhere in the Terminal window and paste (command-V). A TextEdit window will open with the output of the command. If the command produced no output, the window will be empty. Post the contents of the TextEdit window (not the Terminal window), if any — the text, please, not a screenshot. You can then close the TextEdit window. The title of the window doesn't matter, and you don't need to post that. No typing is involved in this step.

Step 2

Repeat with this line:

{ sudo launchctl list | sed 1d | awk '!/0x|com\.(apple|openssh|vix)|org\.(amav|apac|cups|isc|ntp|postf|x)/{print $3}'; sudo defaults read com.apple.loginwindow LoginHook; sudo crontab -l; } 2> /dev/null | open -f -a TextEdit

This time you'll be prompted for your login password, which you do have to type. Nothing will be displayed when you type it. Type it carefully and then press return. You may get a one-time warning to be careful. Heed that warning, but don't post it. If you see a message that your username "is not in the sudoers file," then you're not logged in as an administrator.

Note: If you don’t have a login password, you’ll need to set one before taking this step. If that’s not possible, skip to the next step.

Step 3

{ launchctl list | sed 1d | awk '!/0x|com\.apple|org\.(x|openbsd)/{print $3}'; crontab -l 2> /dev/null; } | open -f -a TextEdit

Step 4

ls -1A /e*/{la,mach}* {,/}L*/{Ad,Compon,Ex,Fram,In,Keyb,La,Mail/Bu,P*P,Priv,Qu,Scripti,Servi,Spo,Sta}* L*/Fonts .la* 2> /dev/null | open -f -a TextEdit

Important: If you formerly synchronized with a MobileMe account, your me.com email address may appear in the output of the above command. If so, anonymize it before posting.

Step 5

osascript -e 'tell application "System Events" to get name of every login item' | open -f -a TextEdit

Remember, steps 1-5 are all copy-and-paste — no typing, except your password. Also remember to post the output.

You can then quit Terminal.

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Answer 8

kijiro.92mac Author

Level 1

0 points

Jul 20, 2013 7:02 PM in response to Linc Davis

Ok, here is the output from the first command:

foo.tap (1.0)

foo.tun (1.0)

Output from the second command:

org.macosforge.xquartz.privileged_startx

com.wdc.WDSmartWareServer

com.wdc.WDDMservice

com.netgear.leafd

com.google.keystone.daemon

com.adobe.fpsaud

From the third:

org.macosforge.xquartz.startx

jp.co.canon.SELPHYCP.BG

com.thursby.pkard.tokendagent

com.netgear.readycloud

com.google.keystone.system.agent

com.akamai.single-user-client

com.adobe.ARM.925793fb327152fd34795896fa1fb9ffa268b2a852256fe56609efa3

From the fourth:

/Library/Components:

/Library/Extensions:

tap.kext

tun.kext

/Library/Frameworks:

AEProfiling.framework

AERegistration.framework

Adobe AIR.framework

AudioMixEngine.framework

Cg.framework

DivX Toolkit.framework

FxPlug.framework

HPDeviceModel.framework

HPPml.framework

HPServicesInterface.framework

HPSmartPrint.framework

NyxAudioAnalysis.framework

PluginManager.framework

ProFX.framework

iLifeFaceRecognition.framework

iLifeKit.framework

iLifePageLayout.framework

iLifeSQLAccess.framework

iLifeSlideshow.framework

iTunesLibrary.framework

/Library/Input Methods:

/Library/Internet Plug-Ins:

AdobePDFViewer.plugin

DirectorShockwave.plugin

Disabled Plug-Ins

DivXBrowserPlugin.plugin

Flash Player.plugin

Flip4Mac WMV Plugin.plugin

Flip4Mac WMV Plugin.webplugin

Google Earth Web Plug-in.plugin

JavaAppletPlugin.plugin

Quartz Composer.webplugin

QuickTime Plugin.plugin

SELPHY Photo Print Plugin.plugin

Scorch.plugin

Silverlight.plugin

flashplayer.xpt

iPhotoPhotocast.plugin

npViewpoint.plugin

npdivx.xpt

nsIQTScriptablePlugin.xpt

/Library/Keyboard Layouts:

/Library/LaunchAgents:

com.canon.SPPHelper.plist

com.google.keystone.agent.plist

com.netgear.readycloud.plist

com.thursby.pkard.tokendagent.plist

jp.co.canon.SELPHYCP.BG.plist

org.macosforge.xquartz.startx.plist

/Library/LaunchDaemons:

com.adobe.fpsaud.plist

com.google.keystone.daemon.plist

com.netgear.leafd.plist

com.wdc.WDDMservice.plist

com.wdc.WDSmartWareServer.plist

org.macosforge.xquartz.privileged_startx.plist

/Library/PreferencePanes:

Flash Player.prefPane

/Library/PrivilegedHelperTools:

/Library/QuickLook:

GBQLGenerator.qlgenerator

iBooksAuthor.qlgenerator

iWork.qlgenerator

/Library/QuickTime:

AppleIntermediateCodec.component

AppleMPEG2Codec.component

DivX Decoder.component

DivX Encoder.component

Flip4Mac WMV Advanced.component

Flip4Mac WMV Export.component

Flip4Mac WMV Import.component

VideoGlide.component

/Library/ScriptingAdditions:

/Library/Spotlight:

GBSpotlightImporter.mdimporter

Microsoft Entourage.mdimporter

Microsoft Office.mdimporter

VMware Virtual Machine.mdimporter

iBooksAuthor.mdimporter

iWeb.mdimporter

iWork.mdimporter

/Library/StartupItems:

ChmodBPF

PKard

VideoGlide Startup

tap

tun

/etc/mach_init.d:

/etc/mach_init_per_login_session.d:

/etc/mach_init_per_user.d:

Library/Address Book Plug-Ins:

SkypeABDialer.bundle

SkypeABSMS.bundle

YMsgrCallABPlugin.bundle

YMsgrMsnABPlugin.bundle

YMsgrSmsABPlugin.bundle

YMsgrYimABPlugin.bundle

Library/Fonts:

Abadi MT Condensed Extra Bold

Abadi MT Condensed Light

Andale Mono

Arial

Arial Black

Arial Narrow

Arial Rounded Bold

Baskerville Old Face

Batang.ttf

Bauhaus 93

Bell MT

Bernard MT Condensed

Book Antiqua

Bookman Old Style

Braggadocio

Britannic Bold

Brush Script

Calisto MT

Century

Century Gothic

Century Schoolbook

Colonna

Comic Sans MS

Cooper Black

Copperplate Gothic Bold

Copperplate Gothic Light

Curlz MT

Desdemona

Edwardian Script ITC

Engravers MT

Eurostile

Footlight Light

Garamond

Georgia

Gill Sans Ultra Bold

Gloucester MT Extra Condensed

Goudy Old Style

Gulim.ttf

Haettenschweiler

Harrington

Impact

Imprint MT Shadow

Kino

Lucida Blackletter

Lucida Bright

Lucida Calligraphy

Lucida Fax

Lucida Handwriting

Lucida Sans

Lucida Sans Typewriter

MS Gothic.ttf

MS Mincho.ttf

MS PGothic.ttf

MS PMincho.ttf

MT Extra

Matura Script Capitals

Mistral

Modern No. 20

Monotype Corsiva

Monotype Sorts

News Gothic MT

Onyx

PMingLiU.ttf

Perpetua Titling MT

Playbill

Rockwell

Rockwell Extra Bold

SimSun.ttf

Stencil

Tahoma

Times New Roman

Trebuchet MS

Verdana

Wide Latin

Wingdings

Wingdings 2

Wingdings 3

encodings.dir

fonts.dir

fonts.list

fonts.scale

Library/InputManagers:

SIMBL

Library/Internet Accounts:

V1

Library/Internet Plug-Ins:

Move-Media-Player.plugin

RealPlayer Plugin.plugin

Unity Player.plugin

fbplugin_1_0_1.plugin

Library/Keyboard Layouts:

Library/LaunchAgents:

com.adobe.ARM.925793fb327152fd34795896fa1fb9ffa268b2a852256fe56609efa3.plist

com.akamai.single-user-client.plist

com.apple.AddressBook.ScheduledSync.PHXCardDAVSource.6E04ED02-439E-4D43-A98D-77E 072C35210.plist

com.apple.AddressBook.ScheduledSync.PHXCardDAVSource.898084A6-CC8C-435E-AB69-63B 6E42E5EF3.plist

com.apple.FolderActions.enabled.plist

com.apple.FolderActions.folders.plist

com.apple.SafariBookmarksSyncer.plist

Library/PreferencePanes:

AkamaiNetSession.prefPane

VLC Streamer.prefPane

And from the fifth:

iTunesHelper, Skype 2, BOINCManager

Thanks!

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Answer 9

Linc Davis

Level 10

209,547 points

Jul 20, 2013 7:30 PM in response to kijiro.92mac

Please read this whole message before doing anything.

This procedure is a test, not a solution. Don’t be disappointed when you find that nothing has changed after you complete it.

Step 1

The purpose of this step is to determine whether the problem is localized to your user account.

Enable guest logins* and log in as Guest. Don't use the Safari-only “Guest User” login created by “Find My Mac.”

While logged in as Guest, you won’t have access to any of your personal files or settings. Applications will behave as if you were running them for the first time. Don’t be alarmed by this; it’s normal. If you need any passwords or other personal data in order to complete the test, memorize, print, or write them down before you begin.

Test while logged in as Guest. Same problem?

After testing, log out of the guest account and, in your own account, disable it if you wish. Any files you created in the guest account will be deleted automatically when you log out of it.

*Note: If you’ve activated “Find My Mac” or FileVault, then you can’t enable the Guest account. The “Guest User” login created by “Find My Mac” is not the same. Create a new account in which to test, and delete it, including its home folder, after testing.

Step 2

The purpose of this step is to determine whether the problem is caused by third-party system modifications that load automatically at startup or login, by a peripheral device, or by corruption of certain system caches.

Disconnect all wired peripherals except those needed for the test, and remove all aftermarket expansion cards. Boot in safe mode and log in to the account with the problem. Note: If FileVault is enabled, or if a firmware password is set, or if the boot volume is a software RAID, you can’t do this. Ask for further instructions.

Safe mode is much slower to boot and run than normal, and some things won’t work at all, including sound output and Wi-Fi on certain iMacs. The next normal boot may also be somewhat slow.

The login screen appears even if you usually log in automatically. You must know your login password in order to log in. If you’ve forgotten the password, you will need to reset it before you begin.

Test while in safe mode. Same problem?

After testing, reboot as usual (i.e., not in safe mode) and verify that you still have the problem. Post the results of steps 1 and 2.

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Answer 10

kijiro.92mac Author

Level 1

0 points

Jul 21, 2013 4:52 AM in response to Linc Davis

Ok, for Step 1:

Creating a new user account I named "Test" and using a non-icloud email account (I used my hotmail account run through the mail program) resulted in the same issues being present as on my primary account. I then deleted the account and it's home folder.

Step 2:

Completed this and the problem was present in safe mode as well. Also persisted when I exited safe mode and logged in normally.

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Answer 11

Linc Davis

Level 10

209,547 points

Jul 21, 2013 9:20 AM in response to kijiro.92mac

Back up all data, then reinstall the OS. You don't need to erase the startup volume, and you won't need your backup unless something goes wrong. If your Mac was upgraded from an older version of OS X, you’ll need the Apple ID and password you used to upgrade.

If you installed the Java runtime distributed by Apple and still need it, you'll have to reinstall it.

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Answer 12

kijiro.92mac Author

Level 1

0 points

Jul 22, 2013 7:09 AM in response to Linc Davis

Alright, thanks for your help. I'm in the process of backing up now and I'll post my findings when I've reinstalled the OS.

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Answer 13

kijiro.92mac Author

Level 1

0 points

Jul 23, 2013 9:11 AM in response to Linc Davis

Ok Linc,

I want to thank you again for your help. I reinstalled the OS and everything seems to work. I'm able to attach files to emails again. The only interesting thing that is happening now is if I change my attachment to be viewed as an icon I can't open it. I haven't tried opening a sent one that's been changed to icon view but I will let you know how that goes.

🙂

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Answer 14

RaphH

Level 1

14 points

Oct 26, 2013 7:28 AM in response to kijiro.92mac

I get the same problem. I have had it before and again with Mavericks. SOLVED IT THIS WAY:

I just use Chrome and then save the pdf file, it opens then perfectly and I can ptint it.

I am not going to do a full reinstall. It is for one file a week!!!

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Answer 15

zmtnbik

Level 1

8 points

Nov 21, 2013 9:55 AM in response to RaphH

Raph...I like your solution much better. Backing up and reinstalling the OS seems like over kill for a minor issue

The issue I continued to have was saving .pdf files from Safari 7.0 to my desk top, trying to open them and receiving the following error: Adobe Reader could not open 'bad.pdf' because it is either not a supported file type or because the file has been damaged (for example, it was sent as an email attachment and wasn't correctly decoded).

Using Chrome instead of Safari, worked w/o issue. Saving the same file using Chrome Version 31.0.1650.57, saves just fine and allows me to open it. I was using Safari in the above example.

I've also verified that FF 25.0.1 works as well.

Mac OS X 10.9

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