MS Remote Desktop for Mac (v8.0.9 - 8.0.12): issue with "Session (ID #) remote control failed."

Hello,
I'm a SysAdmin for a small-med business in CO. We use a cluster of 3 RDS servers that are load-balanced with round-robin DNS and an RD Gateway. When I remote in from a PC, all works as expected. However, when I remote in from my MacPro (my main machine at home)
and try to remote control a user's session, I get this error: 
Note the ID number is unique to the user's RDP session, so will vary each time. 
This is 100% a bug in the "Microsoft Remote Desktop for Mac" program; I am positive of it at this point. 
Does anyone from MS actually monitor these threads at all, or am I wasting my time? Thanks...

Hi,
As this happens with him specific from MRD MAC check whether he is taking RDP with IP address or hostname. Also try to uncheck the Option "Bypass RD Gateway for local address" under RDSH configuration and verify the result. 
Also for more detail he can collect log from MAC side by following path.
Microsoft Remote Desktop>About Microsoft Remote Desktop>Send log via email
Hope it helps!
Thanks.
Dharmesh Solanki
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    [2014-Mar-27 19:48:56] RDP (0): lo0 af=18  addr= netmask=
    [2014-Mar-27 19:48:56] RDP (0): lo0 af=30 (AF_INET6)  addr=::1 netmask=ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff
    [2014-Mar-27 19:48:56] RDP (0): lo0 af=2 (AF_INET)  addr=127.0.0.1 netmask=255.0.0.0
    [2014-Mar-27 19:48:56] RDP (0): lo0 af=30 (AF_INET6)  addr=fe80::1%lo0 netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-27 19:48:56] RDP (0): gif0 af=18  addr= netmask=
    [2014-Mar-27 19:48:56] RDP (0): stf0 af=18  addr= netmask=
    [2014-Mar-27 19:48:56] RDP (0): en0 af=18  addr= netmask=
    [2014-Mar-27 19:48:56] RDP (0): en1 af=18  addr= netmask=
    [2014-Mar-27 19:48:56] RDP (0): en1 af=30 (AF_INET6)  addr=fe80::226:bbff:fe00:c3d7%en1
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    [2014-Mar-27 19:48:56] RDP (0): p2p0 af=18  addr= netmask=
    [2014-Mar-27 19:48:56] RDP (0): utun0 af=18  addr= netmask=
    [2014-Mar-27 19:48:56] RDP (0): utun0 af=30 (AF_INET6)  addr=fe80::e1eb:119:5ad9:da9%utun0
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-27 19:48:56] RDP (0): utun0 af=30 (AF_INET6)  addr=fdce:4b1d:30c:78f8:e1eb:119:5ad9:da9
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-27 19:48:56] RDP (0): --- END INTERFACE LIST ---
    [2014-Mar-27 19:48:56] RDP (0): ----- BEGIN ACTIVE CONNECTION -----
    [2014-Mar-27 19:48:56] RDP (0): client version: 8.0.24428
    [2014-Mar-27 19:48:56] RDP (0): Protocol state changed to: ProtocolConnectingNetwork(1)
    [2014-Mar-27 19:48:56] RDP (0): Resolved '10.1.10.11' to '10.1.10.11' using NameResolveMethod_DNS(1)
    [2014-Mar-27 19:49:04] RDP (0): Protocol state changed to: ProtocolDisconnected(8)
    [2014-Mar-27 19:49:04] RDP (0): ------ END ACTIVE CONNECTION ------
    [2014-Mar-27 19:49:04] RDP (0): --- BEGIN INTERFACE LIST ---
    [2014-Mar-27 19:49:04] RDP (0): lo0 af=18  addr= netmask=
    [2014-Mar-27 19:49:04] RDP (0): lo0 af=30 (AF_INET6)  addr=::1 netmask=ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff
    [2014-Mar-27 19:49:04] RDP (0): lo0 af=2 (AF_INET)  addr=127.0.0.1 netmask=255.0.0.0
    [2014-Mar-27 19:49:04] RDP (0): lo0 af=30 (AF_INET6)  addr=fe80::1%lo0 netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-27 19:49:04] RDP (0): gif0 af=18  addr= netmask=
    [2014-Mar-27 19:49:04] RDP (0): stf0 af=18  addr= netmask=
    [2014-Mar-27 19:49:04] RDP (0): en0 af=18  addr= netmask=
    [2014-Mar-27 19:49:04] RDP (0): en1 af=18  addr= netmask=
    [2014-Mar-27 19:49:04] RDP (0): en1 af=30 (AF_INET6)  addr=fe80::226:bbff:fe00:c3d7%en1
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-27 19:49:04] RDP (0): en1 af=2 (AF_INET)  addr=192.168.0.89 netmask=255.255.255.0
    [2014-Mar-27 19:49:04] RDP (0): fw0 af=18  addr= netmask=
    [2014-Mar-27 19:49:04] RDP (0): p2p0 af=18  addr= netmask=
    [2014-Mar-27 19:49:04] RDP (0): utun0 af=18  addr= netmask=
    [2014-Mar-27 19:49:04] RDP (0): utun0 af=30 (AF_INET6)  addr=fe80::e1eb:119:5ad9:da9%utun0
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-27 19:49:04] RDP (0): utun0 af=30 (AF_INET6)  addr=fdce:4b1d:30c:78f8:e1eb:119:5ad9:da9
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-27 19:49:04] RDP (0): --- END INTERFACE LIST ---
    [2014-Mar-27 19:49:04] RDP (0): ----- BEGIN ACTIVE CONNECTION -----
    [2014-Mar-27 19:49:04] RDP (0): client version: 8.0.24428
    [2014-Mar-27 19:49:05] RDP (0): Protocol state changed to: ProtocolConnectingNetwork(1)
    [2014-Mar-27 19:49:05] RDP (0): Resolved 'javpeds.com' to '70.88.173.126' using NameResolveMethod_DNS(1)
    [2014-Mar-27 19:49:05] RDP (0): Resolved 'javpeds.com' to '70.88.173.126' using NameResolveMethod_DNS(1)
    [2014-Mar-27 19:49:07] RDP (0): Exception caught: Exception in file '../../librdp/private/httpendpoint.cpp' at line 209
        User Message : The gateway failed to connect with the message:
    500 Internal Server Error
    [2014-Mar-27 19:49:07] RDP (0): Exception caught: Exception in file '../../librdp/private/httpendpoint.cpp' at line 209
        User Message : The gateway failed to connect with the message:
    500 Internal Server Error
    [2014-Mar-27 19:49:07] RDP (0): Protocol state changed to: ProtocolDisconnecting(7)
    [2014-Mar-27 19:49:07] RDP (0): Protocol state changed to: ProtocolDisconnected(8)
    [2014-Mar-27 19:49:07] RDP (0): ------ END ACTIVE CONNECTION ------
    [2014-Mar-27 19:49:15] RDP (0): *** Application terminated ***
    [2014-Mar-29 12:03:43] RDP (0): Final rdp configuration used: gatewayhostname:s:javpeds.com
    screen mode id:i:2
    use multimon:i:0
    session bpp:i:24
    full address:s:10.1.10.11
    audiomode:i:2
    username:s:javpeds\ptraquair
    disable wallpaper:i:0
    disable full window drag:i:0
    disable menu anims:i:0
    disable themes:i:0
    alternate shell:s:
    shell working directory:s:
    authentication level:i:2
    connect to console:i:0
    gatewayusagemethod:i:1
    disable cursor setting:i:0
    allow font smoothing:i:1
    allow desktop com"font-family:'SF Cartoonist Hand';font-size:18px;line-height:normal;" />bookmarktype:i:3
    use redirection server name:i:0
    [2014-Mar-29 12:03:43] RDP (0): --- BEGIN INTERFACE LIST ---
    [2014-Mar-29 12:03:43] RDP (0): lo0 af=18  addr= netmask=
    [2014-Mar-29 12:03:43] RDP (0): lo0 af=30 (AF_INET6)  addr=::1 netmask=ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff
    [2014-Mar-29 12:03:43] RDP (0): lo0 af=2 (AF_INET)  addr=127.0.0.1 netmask=255.0.0.0
    [2014-Mar-29 12:03:43] RDP (0): lo0 af=30 (AF_INET6)  addr=fe80::1%lo0 netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:03:43] RDP (0): gif0 af=18  addr= netmask=
    [2014-Mar-29 12:03:43] RDP (0): stf0 af=18  addr= netmask=
    [2014-Mar-29 12:03:43] RDP (0): en0 af=18  addr= netmask=
    [2014-Mar-29 12:03:43] RDP (0): en1 af=18  addr= netmask=
    [2014-Mar-29 12:03:43] RDP (0): en1 af=30 (AF_INET6)  addr=fe80::226:bbff:fe00:c3d7%en1
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:03:43] RDP (0): en1 af=2 (AF_INET)  addr=192.168.1.29 netmask=255.255.255.0
    [2014-Mar-29 12:03:43] RDP (0): fw0 af=18  addr= netmask=
    [2014-Mar-29 12:03:43] RDP (0): p2p0 af=18  addr= netmask=
    [2014-Mar-29 12:03:43] RDP (0): utun0 af=18  addr= netmask=
    [2014-Mar-29 12:03:43] RDP (0): utun0 af=30 (AF_INET6)  addr=fe80::c852:1a8d:126a:a88a%utun0
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:03:43] RDP (0): utun0 af=30 (AF_INET6)  addr=fdce:4b1d:30c:78f8:c852:1a8d:126a:a88a
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:03:43] RDP (0): --- END INTERFACE LIST ---
    [2014-Mar-29 12:03:43] RDP (0): ----- BEGIN ACTIVE CONNECTION -----
    [2014-Mar-29 12:03:43] RDP (0): client version: 8.0.24428
    [2014-Mar-29 12:03:44] RDP (0): Protocol state changed to: ProtocolConnectingNetwork(1)
    [2014-Mar-29 12:03:44] RDP (0): Resolved '10.1.10.11' to '10.1.10.11' using NameResolveMethod_DNS(1)
    [2014-Mar-29 12:03:52] RDP (0): Protocol state changed to: ProtocolDisconnected(8)
    [2014-Mar-29 12:03:52] RDP (0): ------ END ACTIVE CONNECTION ------
    [2014-Mar-29 12:03:52] RDP (0): --- BEGIN INTERFACE LIST ---
    [2014-Mar-29 12:03:52] RDP (0): lo0 af=18  addr= netmask=
    [2014-Mar-29 12:03:52] RDP (0): lo0 af=30 (AF_INET6)  addr=::1 netmask=ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff
    [2014-Mar-29 12:03:52] RDP (0): lo0 af=2 (AF_INET)  addr=127.0.0.1 netmask=255.0.0.0
    [2014-Mar-29 12:03:52] RDP (0): lo0 af=30 (AF_INET6)  addr=fe80::1%lo0 netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:03:52] RDP (0): gif0 af=18  addr= netmask=
    [2014-Mar-29 12:03:52] RDP (0): stf0 af=18  addr= netmask=
    [2014-Mar-29 12:03:52] RDP (0): en0 af=18  addr= netmask=
    [2014-Mar-29 12:03:52] RDP (0): en1 af=18  addr= netmask=
    [2014-Mar-29 12:03:52] RDP (0): en1 af=30 (AF_INET6)  addr=fe80::226:bbff:fe00:c3d7%en1
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:03:52] RDP (0): en1 af=2 (AF_INET)  addr=192.168.1.29 netmask=255.255.255.0
    [2014-Mar-29 12:03:52] RDP (0): fw0 af=18  addr= netmask=
    [2014-Mar-29 12:03:52] RDP (0): p2p0 af=18  addr= netmask=
    [2014-Mar-29 12:03:52] RDP (0): utun0 af=18  addr= netmask=
    [2014-Mar-29 12:03:52] RDP (0): utun0 af=30 (AF_INET6)  addr=fe80::c852:1a8d:126a:a88a%utun0
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:03:52] RDP (0): utun0 af=30 (AF_INET6)  addr=fdce:4b1d:30c:78f8:c852:1a8d:126a:a88a
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:03:52] RDP (0): --- END INTERFACE LIST ---
    [2014-Mar-29 12:03:52] RDP (0): ----- BEGIN ACTIVE CONNECTION -----
    [2014-Mar-29 12:03:52] RDP (0): client version: 8.0.24428
    [2014-Mar-29 12:03:52] RDP (0): Protocol state changed to: ProtocolConnectingNetwork(1)
    [2014-Mar-29 12:03:52] RDP (0): Resolved 'javpeds.com' to '70.88.173.126' using NameResolveMethod_DNS(1)
    [2014-Mar-29 12:03:52] RDP (0): Resolved 'javpeds.com' to '70.88.173.126' using NameResolveMethod_DNS(1)
    [2014-Mar-29 12:03:53] RDP (0): Exception caught: Exception in file '../../librdp/private/httpendpoint.cpp' at line 209
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    500 Internal Server Error
    [2014-Mar-29 12:03:53] RDP (0): Exception caught: Exception in file '../../librdp/private/httpendpoint.cpp' at line 209
        User Message : The gateway failed to connect with the message:
    500 Internal Server Error
    [2014-Mar-29 12:03:53] RDP (0): Protocol state changed to: ProtocolDisconnecting(7)
    [2014-Mar-29 12:03:53] RDP (0): Protocol state changed to: ProtocolDisconnected(8)
    [2014-Mar-29 12:03:53] RDP (0): ------ END ACTIVE CONNECTION ------
    [2014-Mar-29 12:04:24] RDP (0): *** Application terminated ***
    [2014-Mar-29 12:53:47] RDP (0): Final rdp configuration used: gatewayhostname:s:javpeds.com
    screen mode id:i:2
    use multimon:i:0
    session bpp:i:24
    full address:s:10.1.10.11
    audiomode:i:2
    username:s:javpeds\ptraquair
    disable wallpaper:i:0
    disable full window drag:i:0
    disable menu anims:i:0
    disable themes:i:0
    alternate shell:s:
    shell working directory:s:
    authentication level:i:2
    connect to console:i:0
    gatewayusagemethod:i:1
    disable cursor setting:i:0
    allow font smoothing:i:1
    allow desktop com"font-family:'SF Cartoonist Hand';font-size:18px;line-height:normal;" />bookmarktype:i:3
    use redirection server name:i:0
    [2014-Mar-29 12:53:47] RDP (0): --- BEGIN INTERFACE LIST ---
    [2014-Mar-29 12:53:47] RDP (0): lo0 af=18  addr= netmask=
    [2014-Mar-29 12:53:47] RDP (0): lo0 af=30 (AF_INET6)  addr=::1 netmask=ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff
    [2014-Mar-29 12:53:47] RDP (0): lo0 af=2 (AF_INET)  addr=127.0.0.1 netmask=255.0.0.0
    [2014-Mar-29 12:53:47] RDP (0): lo0 af=30 (AF_INET6)  addr=fe80::1%lo0 netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:53:47] RDP (0): gif0 af=18  addr= netmask=
    [2014-Mar-29 12:53:47] RDP (0): stf0 af=18  addr= netmask=
    [2014-Mar-29 12:53:47] RDP (0): en0 af=18  addr= netmask=
    [2014-Mar-29 12:53:47] RDP (0): en1 af=18  addr= netmask=
    [2014-Mar-29 12:53:47] RDP (0): en1 af=30 (AF_INET6)  addr=fe80::226:bbff:fe00:c3d7%en1
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:53:47] RDP (0): en1 af=2 (AF_INET)  addr=10.59.1.176 netmask=255.255.255.0
    [2014-Mar-29 12:53:47] RDP (0): fw0 af=18  addr= netmask=
    [2014-Mar-29 12:53:47] RDP (0): p2p0 af=18  addr= netmask=
    [2014-Mar-29 12:53:47] RDP (0): utun0 af=18  addr= netmask=
    [2014-Mar-29 12:53:47] RDP (0): utun0 af=30 (AF_INET6)  addr=fe80::e590:f4:e6f3:79ee%utun0
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:53:47] RDP (0): utun0 af=30 (AF_INET6)  addr=fdce:4b1d:30c:78f8:e590:f4:e6f3:79ee
    netmask=ffff:ffff:ffff:ffff::
    [2014-Mar-29 12:53:47] RDP (0): --- END INTERFACE LIST ---
    [2014-Mar-29 12:53:47] RDP (0): ----- BEGIN ACTIVE CONNECTION -----
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    [2014-Mar-29 12:53:55] RDP (0): gif0 af=18  addr= netmask=
    [2014-Mar-29 12:53:55] RDP (0): stf0 af=18  addr= netmask=
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