User profile for user: Koothena
Koothena Author
User level: Level 1
4 points

AirDrop ALMOST Working

My Apple Ecosystem Description ("devices" include iOS and Mac OS X hardware):

  1. iMac (Retina 5K, 27-inch, Late 2015), Processor 4 GHz Intel Core i7, Memory 16 GB 1867 MHz DDR3, Storage 3.12 TB Fusion Drive, Mac OS X El Capitan version 10.11.4 (up to date)
  2. iMac (27-inch, Late 2009), Processor 3.06 GHz Intel Core 2 Duo, Memory 16 GB 1067 MHz DDR3, Storage 1 TB SATA Disk, Mac OS X El Capitan 10.11.4 (up to date)
  3. iPad Pro 9.7-inch, Storage 128 GB, iOS 9.3.1 (up to date)
  4. Three identical iPad mini 4 devices, Storage 64 GB, iOS 9.3.1 (up to date)
  5. iPhone 6 Plus, Storage 64 GB, iOS 9.3.1 (up to date)
  6. iPhone 6, Storage 64 GB, iOS 9.3.1 (up to date)


My Question/Issue:

The AirDrop Finder window on the latest iMac (item #1 above) cannot find any of the iOS devices, and none of the iOS devices can find the latest iMac, but all iOS devices can easily/quickly see each other (as expected, the second iMac, #2 above, cannot communicate with any iOS devices as it is too old). However, the Continuity/Hand-Off feature works just fine between iOS devices and the latest iMac, so there is some sort of successful Bluetooth and/or Wi-Fi communication occurring between these iOS and Mac OS devices, but not AirDrop. All devices have AirDrop enabled, set to "Everyone", the two iPhones have their personal hotspots disabled per Apple's official guidance for AirDrop, the iMac's firewall is completely disabled, all devices have been rebooted, Wi-Fi and Bluetooth are enabled on all devices, and yet AirDrop won't work between the latest iMac and the iOS devices.


AirDrop has worked between the iMac and iOS devices in the past, but certainly not consistently as others have noted repeatedly, and I've noticed for perhaps the past month or so it won't work at all for me. However, the latest iMac will find the old iMac when I enable the "Search for an Older Mac" feature in AirDrop, and the older iMac will see the newer iMac as well, yet transfers between them fail with an error message stating "The transfer failed. Please try again." The common denominator to me is the new iMac, but I can't determine what is wrong.


Does anyone in the Apple support community have any suggestions for me to attempt in this regard? Thank you for any assistance you can offer.

iMac (Retina 5K, 27-inch, Late 2015), OS X El Capitan (10.11.4)

Posted on May 8, 2016 9:23 PM

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23 replies
User profile for user: Koothena
Koothena Author
User level: Level 1
4 points

May 8, 2016 9:31 PM in response to Koothena

UPDATE: After posting my question above, I decided to log in to my wife's account on the same iMac that I'm having issues with above, and surprisingly AirDrop found all of our iOS devices with no problem! Additionally, the iMac-to-iMac transfer was successful. Therefore, the AirDrop issue appears to be something tied to my particular user account (both of our accounts are admin-level). This used to work in my account, but now doesn't. What could have changed at an account-level to affect AirDrop?

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User profile for user: Koothena
Koothena Author
User level: Level 1
4 points

May 8, 2016 10:22 PM in response to Linc Davis

Linc Davis, to my knowledge, I'm not using any third-party software that would modify this behavior. Literally, I've installed just a handful of Mac OS apps since purchasing the Mac late last year:

  • 1Password
  • Adobe Creative Cloud (Lightroom + Photoshop)
  • BitTorrent Sync
  • Dropbox
  • Google Earth
  • Omnifocus
  • Spotify
  • VLC
  • Xcode


None of these jump out at me as having an issue.

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User profile for user: Linc Davis
Linc Davis
User level: Level 10
209,739 points

May 8, 2016 10:33 PM in response to Koothena

Please launch the Console application in any one 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 and start typing the name.

The title of the Console window should be All Messages. If it isn't, select

SYSTEM LOG QUERIES ▹ All Messages

from the log list on the left. If you don't see that list, select

View ▹ Show Log List

from the menu bar at the top of the screen.

Click the Clear Display icon in the toolbar. Then take an action that isn't working the way you expect. Select any lines that appear in the Console window. Copy them to the Clipboard by pressing the key combination command-C. Paste into a reply to this message by pressing command-V.

The log contains a vast amount of information, almost all of which is irrelevant to solving any particular problem. When posting a log extract, be selective. A few dozen lines are almost always more than enough.

Please don't indiscriminately dump thousands of lines from the log into this discussion.

Please don't post screenshots of log messages—post the text.

Some private information, such as your name or email address, may appear in the log. Anonymize before posting.

When you post the log extract, you might see an error message on the web page: "You have included content in your post that is not permitted," or "The message contains invalid characters." That's a bug in the forum software. Please post the text on Pastebin, then post a link here to the page you created.

If you have an account on Pastebin, please don't select Private from the Paste Exposure menu on the page, because then no one but you will be able to see it.

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User profile for user: Koothena
Koothena Author
User level: Level 1
4 points

May 8, 2016 11:03 PM in response to Linc Davis

Linc Davis, I've followed your steps, and I have a quick question. Even after I clear the display and then perform my action of bringing up AirDrop in Finder, the "new" logs that appear have the timestamp of almost three days ago. For example, after clearing the display and visually seeing the data clear out, I brought up AirDrop and saw events starting timestamp of 5/6/16, 6:47:40 AM even though my local time is 5/9/16 12:59:XX AM CDT. I'm not sure that the data I'll be copying/pasting is what is current, do you experience the same thing in the Console app?

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User profile for user: Koothena
Koothena Author
User level: Level 1
4 points

May 8, 2016 11:17 PM in response to Koothena

Linc Davis, thank you for the console suggestion, I see some interesting info there (see below). From what I can gather from these logs, it is detecting both of the devices I tried to connect with during the console session (Jason's iPad and Jason's iPhone), yet the connection failed because a secure connection could not be made. Some handshaking also failed.


5/9/16 1:10:12.000 AM kernel[0]: ARPT: 9860.883847: AWDL Sync Enabled 1, data path state[1]

5/9/16 1:10:12.686 AM sharingd[281]: 01:10:12.685 : Bonjour discovery started

5/9/16 1:10:12.686 AM sharingd[281]: 01:10:12.686 : Finder entered AirDrop

5/9/16 1:10:12.686 AM sharingd[281]: 01:10:12.686 : BTLE scanning stopped

5/9/16 1:10:12.686 AM sharingd[281]: 01:10:12.686 : BTLE scanning started

5/9/16 1:10:12.687 AM sharingd[281]: 01:10:12.686 : Scanning mode Everyone

5/9/16 1:10:12.695 AM sharingd[281]: 01:10:12.695 : BTLE advertiser Powered On

5/9/16 1:10:12.696 AM sharingd[281]: 01:10:12.696 : BTLE advertising hashes <01acd15c 61a98000 0000>

5/9/16 1:10:12.697 AM sharingd[281]: 01:10:12.696 : BTLE scanner Powered On

5/9/16 1:10:13.312 AM sharingd[281]: 01:10:13.312 : Bonjour discovered e78b2991955c over awdl0

5/9/16 1:10:13.373 AM sharingd[281]: 01:10:13.373 : Bonjour discovered e78b2991955c TXT record

5/9/16 1:10:13.373 AM sharingd[281]: 01:10:13.373 : Bonjour resolving e78b2991955c service over 0

5/9/16 1:10:13.375 AM sharingd[281]: 01:10:13.375 : Bonjour resolved e78b2991955c over awdl0

5/9/16 1:10:13.375 AM sharingd[281]: 01:10:13.375 : Connecting to e78b2991955c at [Jasons-iPad.local]:8770

5/9/16 1:10:13.471 AM sharingd[281]: 01:10:13.470 : Sending client certificate to e78b2991955c

5/9/16 1:10:13.487 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:13.515 AM sharingd[281]: 01:10:13.514 : Sending client certificate to e78b2991955c

5/9/16 1:10:13.521 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:13.549 AM sharingd[281]: 01:10:13.549 : Sending client certificate to e78b2991955c

5/9/16 1:10:13.555 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:13.586 AM sharingd[281]: 01:10:13.586 : Sending client certificate to e78b2991955c

5/9/16 1:10:13.592 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:13.592 AM sharingd[281]: NSURLSession/NSURLConnection HTTP load failed (kCFStreamErrorDomainSSL, -67808)

5/9/16 1:10:13.593 AM sharingd[281]: 01:10:13.592 : Connection to e78b2991955c failed (Error Domain=NSURLErrorDomain Code=-1200 "An SSL error has occurred and a secure connection to the server cannot be made." UserInfo={NSURLErrorFailingURLPeerTrustErrorKey=<SecTrust 0x7f8993e4a6e0 [0x7fff74c19440]>, NSLocalizedRecoverySuggestion=Would you like to connect to the server anyway?, _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808, NSErrorPeerCertificateChainKey=(

"<SecCertificate 0x7f8993d36cb0 [0x7fff74c19440]>",

"<SecCertificate 0x7f89927b21e0 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993db6360 [0x7fff74c19440]>"

), NSUnderlyingError=0x7f8993f646b0 {Error Domain=kCFErrorDomainCFNetwork Code=-1200 "(null)" UserInfo={_kCFNetworkCFStreamSSLErrorOriginalValue=-67808, kCFStreamPropertySSLPeerCertificates=(

"<SecCertificate 0x7f8993d36cb0 [0x7fff74c19440]>",

"<SecCertificate 0x7f89927b21e0 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993db6360 [0x7fff74c19440]>"

), _kCFStreamPropertySSLClientCertificateState=2, kCFStreamPropertySSLPeerTrust=<SecTrust 0x7f8993e4a6e0 [0x7fff74c19440]>, _kCFStreamPropertySSLClientCertificates=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993e98160 [0x7fff74c19440]>"

), _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808}}, NSErrorClientCertificateChainKey=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993e98160 [0x7fff74c19440]>"

), NSLocalizedDescription=An SSL error has occurred and a secure connection to the server cannot be made., NSErrorFailingURLKey=https://jasons-ipad.local:8770/Discover, NSErrorFailingURLStringKey=https://jasons-ipad.local:8770/Discover, NSErrorClientCertificateStateKey=2})

5/9/16 1:10:13.939 AM sharingd[281]: 01:10:13.938 : Retry discovery request for e78b2991955c

5/9/16 1:10:13.939 AM sharingd[281]: 01:10:13.938 : Bonjour resolving e78b2991955c service over 0

5/9/16 1:10:13.940 AM sharingd[281]: 01:10:13.940 : Bonjour resolved e78b2991955c over awdl0

5/9/16 1:10:13.941 AM sharingd[281]: 01:10:13.940 : Connecting to e78b2991955c at [Jasons-iPad.local]:8770

5/9/16 1:10:13.999 AM sharingd[281]: 01:10:13.998 : Sending client certificate to e78b2991955c

5/9/16 1:10:14.005 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:14.033 AM sharingd[281]: 01:10:14.032 : Sending client certificate to e78b2991955c

5/9/16 1:10:14.039 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:14.068 AM sharingd[281]: 01:10:14.068 : Sending client certificate to e78b2991955c

5/9/16 1:10:14.074 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:14.110 AM sharingd[281]: 01:10:14.110 : Sending client certificate to e78b2991955c

5/9/16 1:10:14.118 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:14.119 AM sharingd[281]: NSURLSession/NSURLConnection HTTP load failed (kCFStreamErrorDomainSSL, -67808)

5/9/16 1:10:14.119 AM sharingd[281]: 01:10:14.119 : Connection to e78b2991955c failed (Error Domain=NSURLErrorDomain Code=-1200 "An SSL error has occurred and a secure connection to the server cannot be made." UserInfo={NSURLErrorFailingURLPeerTrustErrorKey=<SecTrust 0x7f899243b4b0 [0x7fff74c19440]>, NSLocalizedRecoverySuggestion=Would you like to connect to the server anyway?, _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808, NSErrorPeerCertificateChainKey=(

"<SecCertificate 0x7f8993a3e9b0 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993a3ec00 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993a3ee50 [0x7fff74c19440]>"

), NSUnderlyingError=0x7f8993e13de0 {Error Domain=kCFErrorDomainCFNetwork Code=-1200 "(null)" UserInfo={_kCFNetworkCFStreamSSLErrorOriginalValue=-67808, kCFStreamPropertySSLPeerCertificates=(

"<SecCertificate 0x7f8993a3e9b0 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993a3ec00 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993a3ee50 [0x7fff74c19440]>"

), _kCFStreamPropertySSLClientCertificateState=2, kCFStreamPropertySSLPeerTrust=<SecTrust 0x7f899243b4b0 [0x7fff74c19440]>, _kCFStreamPropertySSLClientCertificates=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f57470 [0x7fff74c19440]>"

), _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808}}, NSErrorClientCertificateChainKey=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f57470 [0x7fff74c19440]>"

), NSLocalizedDescription=An SSL error has occurred and a secure connection to the server cannot be made., NSErrorFailingURLKey=https://jasons-ipad.local:8770/Discover, NSErrorFailingURLStringKey=https://jasons-ipad.local:8770/Discover, NSErrorClientCertificateStateKey=2})

5/9/16 1:10:15.129 AM sharingd[281]: 01:10:15.129 : Retry discovery request for e78b2991955c

5/9/16 1:10:15.130 AM sharingd[281]: 01:10:15.129 : Bonjour resolving e78b2991955c service over 0

5/9/16 1:10:15.133 AM sharingd[281]: 01:10:15.132 : Bonjour resolved e78b2991955c over awdl0

5/9/16 1:10:15.133 AM sharingd[281]: 01:10:15.132 : Connecting to e78b2991955c at [Jasons-iPad.local]:8770

5/9/16 1:10:15.819 AM sharingd[281]: 01:10:15.818 : Sending client certificate to e78b2991955c

5/9/16 1:10:15.825 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:15.855 AM sharingd[281]: 01:10:15.854 : Sending client certificate to e78b2991955c

5/9/16 1:10:15.861 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:15.889 AM sharingd[281]: 01:10:15.888 : Sending client certificate to e78b2991955c

5/9/16 1:10:15.895 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:15.924 AM sharingd[281]: 01:10:15.923 : Sending client certificate to e78b2991955c

5/9/16 1:10:15.930 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:15.930 AM sharingd[281]: NSURLSession/NSURLConnection HTTP load failed (kCFStreamErrorDomainSSL, -67808)

5/9/16 1:10:15.931 AM sharingd[281]: 01:10:15.930 : Connection to e78b2991955c failed (Error Domain=NSURLErrorDomain Code=-1200 "An SSL error has occurred and a secure connection to the server cannot be made." UserInfo={NSURLErrorFailingURLPeerTrustErrorKey=<SecTrust 0x7f8993e4d0c0 [0x7fff74c19440]>, NSLocalizedRecoverySuggestion=Would you like to connect to the server anyway?, _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808, NSErrorPeerCertificateChainKey=(

"<SecCertificate 0x7f8993e4c6c0 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993e6d440 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993e4cb30 [0x7fff74c19440]>"

), NSUnderlyingError=0x7f89925022b0 {Error Domain=kCFErrorDomainCFNetwork Code=-1200 "(null)" UserInfo={_kCFNetworkCFStreamSSLErrorOriginalValue=-67808, kCFStreamPropertySSLPeerCertificates=(

"<SecCertificate 0x7f8993e4c6c0 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993e6d440 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993e4cb30 [0x7fff74c19440]>"

), _kCFStreamPropertySSLClientCertificateState=2, kCFStreamPropertySSLPeerTrust=<SecTrust 0x7f8993e4d0c0 [0x7fff74c19440]>, _kCFStreamPropertySSLClientCertificates=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f61270 [0x7fff74c19440]>"

), _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808}}, NSErrorClientCertificateChainKey=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f61270 [0x7fff74c19440]>"

), NSLocalizedDescription=An SSL error has occurred and a secure connection to the server cannot be made., NSErrorFailingURLKey=https://jasons-ipad.local:8770/Discover, NSErrorFailingURLStringKey=https://jasons-ipad.local:8770/Discover, NSErrorClientCertificateStateKey=2})

5/9/16 1:10:18.442 AM sharingd[281]: 01:10:18.441 : Retry discovery request for e78b2991955c

5/9/16 1:10:18.442 AM sharingd[281]: 01:10:18.441 : Bonjour resolving e78b2991955c service over 0

5/9/16 1:10:18.444 AM sharingd[281]: 01:10:18.443 : Bonjour resolved e78b2991955c over awdl0

5/9/16 1:10:18.444 AM sharingd[281]: 01:10:18.443 : Connecting to e78b2991955c at [Jasons-iPad.local]:8770

5/9/16 1:10:18.529 AM sharingd[281]: 01:10:18.528 : Sending client certificate to e78b2991955c

5/9/16 1:10:18.545 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:18.574 AM sharingd[281]: 01:10:18.574 : Sending client certificate to e78b2991955c

5/9/16 1:10:18.581 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:18.610 AM sharingd[281]: 01:10:18.609 : Sending client certificate to e78b2991955c

5/9/16 1:10:18.616 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:18.644 AM sharingd[281]: 01:10:18.643 : Sending client certificate to e78b2991955c

5/9/16 1:10:18.650 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:18.650 AM sharingd[281]: NSURLSession/NSURLConnection HTTP load failed (kCFStreamErrorDomainSSL, -67808)

5/9/16 1:10:18.650 AM sharingd[281]: 01:10:18.650 : Connection to e78b2991955c failed (Error Domain=NSURLErrorDomain Code=-1200 "An SSL error has occurred and a secure connection to the server cannot be made." UserInfo={NSURLErrorFailingURLPeerTrustErrorKey=<SecTrust 0x7f8993f40b80 [0x7fff74c19440]>, NSLocalizedRecoverySuggestion=Would you like to connect to the server anyway?, _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808, NSErrorPeerCertificateChainKey=(

"<SecCertificate 0x7f8993f53780 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f00a40 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f60ff0 [0x7fff74c19440]>"

), NSUnderlyingError=0x7f8993a310d0 {Error Domain=kCFErrorDomainCFNetwork Code=-1200 "(null)" UserInfo={_kCFNetworkCFStreamSSLErrorOriginalValue=-67808, kCFStreamPropertySSLPeerCertificates=(

"<SecCertificate 0x7f8993f53780 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f00a40 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f60ff0 [0x7fff74c19440]>"

), _kCFStreamPropertySSLClientCertificateState=2, kCFStreamPropertySSLPeerTrust=<SecTrust 0x7f8993f40b80 [0x7fff74c19440]>, _kCFStreamPropertySSLClientCertificates=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993e50a00 [0x7fff74c19440]>"

), _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808}}, NSErrorClientCertificateChainKey=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993e50a00 [0x7fff74c19440]>"

), NSLocalizedDescription=An SSL error has occurred and a secure connection to the server cannot be made., NSErrorFailingURLKey=https://jasons-ipad.local:8770/Discover, NSErrorFailingURLStringKey=https://jasons-ipad.local:8770/Discover, NSErrorClientCertificateStateKey=2})

5/9/16 1:10:26.084 AM sharingd[281]: 01:10:26.083 : Retry discovery request for e78b2991955c

5/9/16 1:10:26.084 AM sharingd[281]: 01:10:26.083 : Bonjour resolving e78b2991955c service over 0

5/9/16 1:10:26.086 AM sharingd[281]: 01:10:26.085 : Bonjour resolved e78b2991955c over awdl0

5/9/16 1:10:26.086 AM sharingd[281]: 01:10:26.085 : Connecting to e78b2991955c at [Jasons-iPad.local]:8770

5/9/16 1:10:26.303 AM sharingd[281]: 01:10:26.302 : Sending client certificate to e78b2991955c

5/9/16 1:10:26.309 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:26.869 AM sharingd[281]: 01:10:26.868 : Sending client certificate to e78b2991955c

5/9/16 1:10:26.875 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:26.946 AM sharingd[281]: 01:10:26.945 : Sending client certificate to e78b2991955c

5/9/16 1:10:26.952 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:27.196 AM sharingd[281]: 01:10:27.196 : Sending client certificate to e78b2991955c

5/9/16 1:10:27.212 AM sharingd[281]: CFNetwork SSLHandshake failed (-67808)

5/9/16 1:10:27.212 AM sharingd[281]: NSURLSession/NSURLConnection HTTP load failed (kCFStreamErrorDomainSSL, -67808)

5/9/16 1:10:27.212 AM sharingd[281]: 01:10:27.212 : Connection to e78b2991955c failed (Error Domain=NSURLErrorDomain Code=-1200 "An SSL error has occurred and a secure connection to the server cannot be made." UserInfo={NSURLErrorFailingURLPeerTrustErrorKey=<SecTrust 0x7f89970466a0 [0x7fff74c19440]>, NSLocalizedRecoverySuggestion=Would you like to connect to the server anyway?, _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808, NSErrorPeerCertificateChainKey=(

"<SecCertificate 0x7f89926e5500 [0x7fff74c19440]>",

"<SecCertificate 0x7f89926e5750 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f08fc0 [0x7fff74c19440]>"

), NSUnderlyingError=0x7f8993c94400 {Error Domain=kCFErrorDomainCFNetwork Code=-1200 "(null)" UserInfo={_kCFNetworkCFStreamSSLErrorOriginalValue=-67808, kCFStreamPropertySSLPeerCertificates=(

"<SecCertificate 0x7f89926e5500 [0x7fff74c19440]>",

"<SecCertificate 0x7f89926e5750 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f08fc0 [0x7fff74c19440]>"

), _kCFStreamPropertySSLClientCertificateState=2, kCFStreamPropertySSLPeerTrust=<SecTrust 0x7f89970466a0 [0x7fff74c19440]>, _kCFStreamPropertySSLClientCertificates=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8997047880 [0x7fff74c19440]>"

), _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808}}, NSErrorClientCertificateChainKey=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8997047880 [0x7fff74c19440]>"

), NSLocalizedDescription=An SSL error has occurred and a secure connection to the server cannot be made., NSErrorFailingURLKey=https://jasons-ipad.local:8770/Discover, NSErrorFailingURLStringKey=https://jasons-ipad.local:8770/Discover, NSErrorClientCertificateStateKey=2})

5/9/16 1:10:27.212 AM sharingd[281]: 01:10:27.212 : SDWormholeClient Error Domain=NSURLErrorDomain Code=-1200 "An SSL error has occurred and a secure connection to the server cannot be made." UserInfo={NSURLErrorFailingURLPeerTrustErrorKey=<SecTrust 0x7f89970466a0 [0x7fff74c19440]>, NSLocalizedRecoverySuggestion=Would you like to connect to the server anyway?, _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808, NSErrorPeerCertificateChainKey=(

"<SecCertificate 0x7f89926e5500 [0x7fff74c19440]>",

"<SecCertificate 0x7f89926e5750 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f08fc0 [0x7fff74c19440]>"

), NSUnderlyingError=0x7f8993c94400 {Error Domain=kCFErrorDomainCFNetwork Code=-1200 "(null)" UserInfo={_kCFNetworkCFStreamSSLErrorOriginalValue=-67808, kCFStreamPropertySSLPeerCertificates=(

"<SecCertificate 0x7f89926e5500 [0x7fff74c19440]>",

"<SecCertificate 0x7f89926e5750 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993f08fc0 [0x7fff74c19440]>"

), _kCFStreamPropertySSLClientCertificateState=2, kCFStreamPropertySSLPeerTrust=<SecTrust 0x7f89970466a0 [0x7fff74c19440]>, _kCFStreamPropertySSLClientCertificates=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8997047880 [0x7fff74c19440]>"

), _kCFStreamErrorDomainKey=3, _kCFStreamErrorCodeKey=-67808}}, NSErrorClientCertificateChainKey=(

"<SecIdentity 0x7f899251a270 [0x7fff74c19440]>",

"<SecCertificate 0x7f8993951d80 [0x7fff74c19440]>",

"<SecCertificate 0x7f8997047880 [0x7fff74c19440]>"

), NSLocalizedDescription=An SSL error has occurred and a secure connection to the server cannot be made., NSErrorFailingURLKey=https://jasons-ipad.local:8770/Discover, NSErrorFailingURLStringKey=https://jasons-ipad.local:8770/Discover, NSErrorClientCertificateStateKey=2}

5/9/16 1:10:27.678 AM sharingd[281]: 01:10:27.678 : Bonjour discovered fd09a44343cf over awdl0

5/9/16 1:10:28.137 AM sharingd[281]: 01:10:28.136 : Bonjour discovered fd09a44343cf TXT record

5/9/16 1:10:28.137 AM sharingd[281]: 01:10:28.136 : Bonjour resolving fd09a44343cf service over 0

5/9/16 1:10:29.781 AM sharingd[281]: 01:10:29.780 : Bonjour resolved fd09a44343cf over awdl0

5/9/16 1:10:29.781 AM sharingd[281]: 01:10:29.780 : Connecting to fd09a44343cf at [Jasons-iPhone.local]:8770

5/9/16 1:10:44.781 AM sharingd[281]: 01:10:44.781 : Connection to fd09a44343cf failed (Error Domain=NSURLErrorDomain Code=-1001 "The request timed out." UserInfo={NSUnderlyingError=0x7f8993cda790 {Error Domain=kCFErrorDomainCFNetwork Code=-1001 "(null)" UserInfo={_kCFStreamErrorCodeKey=-2102, _kCFStreamErrorDomainKey=4}}, NSErrorFailingURLStringKey=https://jasons-iphone.local:8770/Discover, NSErrorFailingURLKey=https://jasons-iphone.local:8770/Discover, _kCFStreamErrorDomainKey=4, _kCFStreamErrorCodeKey=-2102, NSLocalizedDescription=The request timed out.})

5/9/16 1:10:45.145 AM sharingd[281]: 01:10:45.145 : Retry discovery request for fd09a44343cf

5/9/16 1:10:45.145 AM sharingd[281]: 01:10:45.145 : Bonjour resolving fd09a44343cf service over 0

5/9/16 1:10:45.149 AM sharingd[281]: 01:10:45.148 : Bonjour resolved fd09a44343cf over awdl0

5/9/16 1:10:45.149 AM sharingd[281]: 01:10:45.148 : Connecting to fd09a44343cf at [Jasons-iPhone.local]:8770

5/9/16 1:11:00.150 AM sharingd[281]: 01:11:00.149 : Connection to fd09a44343cf failed (Error Domain=NSURLErrorDomain Code=-1001 "The request timed out." UserInfo={NSUnderlyingError=0x7f89939a8380 {Error Domain=kCFErrorDomainCFNetwork Code=-1001 "(null)" UserInfo={_kCFStreamErrorCodeKey=-2102, _kCFStreamErrorDomainKey=4}}, NSErrorFailingURLStringKey=https://jasons-iphone.local:8770/Discover, NSErrorFailingURLKey=https://jasons-iphone.local:8770/Discover, _kCFStreamErrorDomainKey=4, _kCFStreamErrorCodeKey=-2102, NSLocalizedDescription=The request timed out.})

5/9/16 1:11:01.106 AM sharingd[281]: 01:11:01.105 : Retry discovery request for fd09a44343cf

5/9/16 1:11:01.106 AM sharingd[281]: 01:11:01.105 : Bonjour resolving fd09a44343cf service over 0

5/9/16 1:11:01.108 AM sharingd[281]: 01:11:01.107 : Bonjour resolved fd09a44343cf over awdl0

5/9/16 1:11:01.108 AM sharingd[281]: 01:11:01.107 : Connecting to fd09a44343cf at [Jasons-iPhone.local]:8770

Reply
User profile for user: Linc Davis
Linc Davis
User level: Level 10
209,739 points

May 9, 2016 6:11 AM in response to Koothena

Please back up all data.

Launch the Keychain Access 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 and start typing the name.

From the Category list in the lower left corner of the window, select My Certificates. In the list of certificates on the right, there may be one or more have a name that begins with "VeriSign". Export each such certificate by dragging it to the Desktop, then delete it from the keychain. If there are any certificates marked with a red "X" as expired or invalid, regardless of name, delete them without exporting.

Next, select Certificates from the Category list. Look carefully at the list of certificates in the right side of the window. If any of them has a blue-and-white plus sign in the icon, double-click it. An inspection window will open. Click the disclosure triangle labeled Trust to disclose the trust settings for the certificate. From the menu labeled

Secure Sockets Layer (SSL)

select

no value specified

Close the inspection window. You'll be prompted for your administrator password to update the settings.

Now open the same inspection window again, and select

When using this certificate: Use System Defaults

Save the change in the same way as before.

Revert all the certificates with non-default trust settings. Never again change any of those settings.

Again, delete all expired or invalid certificates.

Log out or restart the computer. Test. If all is now well, back up again, then delete the certificates you exported to the Desktop.

Reply
User profile for user: Koothena
Koothena Author
User level: Level 1
4 points

May 9, 2016 6:51 PM in response to Linc Davis

Linc Davis,


Thank you again for your suggestion on certificates. Unfortunately, I believe all is in order there. I say this because I only have two certificates under My Certificates (one regarding my Apple ID, and another regarding my iPhone Developer dabbling). Under Certificates, there is one more regarding Apple Application Integration Certification Authority. All three certificates are marked as valid, have start dates in the past, and expiration dates in the future. All three also already have no value specified in all their trust fields and Use System Defaults set as well. I didn't have to change anything and there were no certificates to throw away.


Reviewing the certificates has me wondering about something, and that is my dabbling in iOS development with Xcode. My certificate for that became valid presumably on the day I started my coding, which the certificate states as March 28, 2016, which falls into the "recent months" that I noticed AirDrop not working. The private key details for the iPhone Development certificate differs from the Apple ID private key details in that the former has restrictions in its Access Control settings while the latter does not -- perhaps that is perfectly fine, but it is a difference. I will now compare the certificates in my wife's account to mine, and perhaps do some experimentation after making backups. Any thoughts now?

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User profile for user: Linc Davis
Linc Davis
User level: Level 10
209,739 points

May 9, 2016 7:14 PM in response to Koothena

Please back up all data, then open the Library folder in your home folder by holding down the option key and selecting

Go ▹ Library

from the Finder menu bar.

Inside the Library folder is a subfolder named "Keychains." Move that folder to the Desktop. Log out or restart the computer.

Test. You may be prompted for some passwords that you don't normally have to enter.

After testing, put the folder that you moved back where it was, overwriting the one that will have been created in its place. Log out or restart again and post your results.

Reply
User profile for user: Koothena
Koothena Author
User level: Level 1
4 points

May 9, 2016 7:33 PM in response to Linc Davis

Linc Davis, PROGRESS! After moving the Keychains folder to the desktop and restarting, the AirDrop folder in Finder easily found my iPhone and iPad that I'm testing with this evening. I then deleted the newly-created Keychains folder and moved the Keychains folder from my Desktop back to the Library (rather than simply overwriting since I didn't know if the file list of the two folders would be merged or not rather than simply replaced). I restarted again and observed the same, bad behavior as before.


Therefore, what would you recommend at this point? Can I simply blow away my Keychains folder and start from scratch?


(Side note: This experiment did bring back an old error message that I've seen before stating "This Mac can't connect to iCloud because of a problem with <my email>. Open iCloud preferences to fix this problem." Previous attempts to fix this by entering my password don't work, it never accepts my password, though if I enter a bad one it complains. In the end, all my iCloud functionality works still and the error eventually went away. I've often wondered if this has something to do with two iMacs using the same iCloud account.)

Reply
User profile for user: Linc Davis
Linc Davis
User level: Level 10
209,739 points

May 9, 2016 7:58 PM in response to Koothena

This procedure is a diagnostic test. It makes no changes to your data.

Please triple-click anywhere in the line below on this page to select it:

ls -@BOaen L*/Keyc* | pbcopy

Copy the selected text to the Clipboard by pressing the key combination command-C.

Launch the built-in Terminal application in any one 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 and start typing the name.

Paste into the Terminal window by pressing the key combination command-V. I've tested these instructions only with the Safari web browser. If you use another browser, you may have to press the return key after pasting.

Wait for a new line ending in a dollar sign ($) to appear below what you entered.

The output of the command will be automatically copied to the Clipboard. If the command produced no output, the Clipboard will be empty. Paste into a reply to this message.

The Terminal window doesn't show the output. Please don't copy anything from there.

If any personal information appears in the output, anonymize before posting, but don’t remove the context.

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User profile for user: Koothena
Koothena Author
User level: Level 1
4 points

May 9, 2016 8:01 PM in response to Linc Davis

Linc Davis, per your request, here is the output:


total 1896

drwxr-xr-x 11 501 20 - 374 May 9 21:59 .

drwx------@ 64 501 20 hidden 2176 May 9 21:24 ..

com.apple.FinderInfo 32

0: ABCDEFAB-CDEF-ABCD-EFAB-CDEF0000000C deny delete

-r-------- 1 501 20 - 0 Nov 1 2015 .fl0D1D1BA9

-r--r--r-- 1 501 20 - 0 Oct 31 2015 .fl62323D2F

drwx------ 7 501 20 - 238 Mar 21 22:41 17589A68-B124-54BA-9D98-6B5F51F5C697

-rw-r--r-- 1 501 20 - 277 Dec 1 22:37 47B3CB7C-0352-4D7D-87B6-43E188F424B6

-rw-r--r-- 1 501 20 - 36 Oct 31 2015 breadcrumbIdentifier

-rw-r--r--@ 1 501 20 - 336472 May 9 21:59 login.keychain

com.apple.quarantine 21

-rw-r--r--@ 1 501 20 - 212260 Dec 1 22:28 login_renamed_1.keychain

com.apple.quarantine 29

-rw-r--r--@ 1 501 20 - 68608 Dec 1 22:33 login_renamed_2.keychain

com.apple.quarantine 21

-rw------- 1 501 20 - 337812 May 9 13:54 metadata.keychain

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