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Remote session via RDGW fine with Windows - not possible with Mac ...?

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Hi,

I've configured a fresh single RDS Server (all roles on one Server including Gateway) based on Windows Server 2012 R2. Everything works fine when we use Windows 7 with current RDP Client to connect via Gateway/HTTPS.

When we use a Mac (OS X 10.9.3) with current Version of "Microsoft Remote Desktop" (8.0.7), no RDP Connection is established. Error message: "Unable to connect to remote PC. Please verify ...". Login on <external.domain.name>/rdweb works fine and I'm able to download the .rdp-file and open it with Microsoft Remote Desktop, but after a few seconds the error above appears.

I did some traffic analyzing on our Firewall and it seems that the Mac try to connect on port 3389 on the public ip of the RDS Server, which is blocked. I manually configured a RDP Connection with Gateway - same error. The log of Microsoft Remote Desktop:

[2014-May-22 11:58:30] RDP (0): Final rdp configuration used: gatewayhostname:s:<external.domain.name>

screen mode id:i:2

use multimon:i:1

session bpp:i:32

full address:s:<external.domain.name>

audiomode:i:0

username:s:

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:1

redirectprinters:i:1

bookmarktype:i:3

use redirection server name:i:1

loadbalanceinfo:s:tsv://MS Terminal Services Plugin.1.<name>_RDS

[2014-May-22 11:58:30] RDP (0): --- BEGIN INTERFACE LIST ---

[2014-May-22 11:58:30] RDP (0): lo0 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): lo0 af=30 (AF_INET6)  addr=::1 netmask=ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff

[2014-May-22 11:58:30] RDP (0): lo0 af=2 (AF_INET)  addr=127.0.0.1 netmask=255.0.0.0

[2014-May-22 11:58:30] RDP (0): lo0 af=30 (AF_INET6)  addr=fe80::1%lo0 netmask=ffff:ffff:ffff:ffff::

[2014-May-22 11:58:30] RDP (0): gif0 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): stf0 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): en0 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): en0 af=30 (AF_INET6)  addr=<address>%en0 netmask=ffff:ffff:ffff:ffff::

[2014-May-22 11:58:30] RDP (0): en0 af=2 (AF_INET)  addr=<address> netmask=255.255.255.0

[2014-May-22 11:58:30] RDP (0): en0 af=2 (AF_INET)  addr=<address> netmask=255.255.255.0

[2014-May-22 11:58:30] RDP (0): en1 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): fw0 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): en2 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): bridge0 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): p2p0 af=18  addr= netmask=

[2014-May-22 11:58:30] RDP (0): --- END INTERFACE LIST ---

[2014-May-22 11:58:30] RDP (0): ----- BEGIN ACTIVE CONNECTION -----

[2014-May-22 11:58:30] RDP (0): client version: 8.0.24875

[2014-May-22 11:58:30] RDP (0): Protocol state changed to: ProtocolConnectingNetwork(1)

[2014-May-22 11:58:30] RDP (0): correlation id: 7a0a5e55-c35a-c642-882e-788a487a0000

[2014-May-22 11:58:30] RDP (0): Resolved '<external.domain.name>' to '<external ip address>' using NameResolveMethod_DNS(1)

[2014-May-22 11:58:38] RDP (0): Protocol state changed to: ProtocolDisconnected(8)

[2014-May-22 11:58:38] RDP (0): ------ END ACTIVE CONNECTION ------

I remember that there was an issue to establish SSO based on DNS resolve (external Domain Name to internal ip address via Gateway Connection); but we resolved this with a new DNS Zone. But why is it fine on Windows, but not on Mac OS X with Microsoft Remote Desktop? I wondering why the MRD is not using the Gateway Connection to resolve the RDP host ... ?

Many thanks,

Erik


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