Remote Desktop app for iMac to Windows server?
Remote Desktop app for iMac to Windows server?
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clockworks

Original Poster:

7,723 posts

175 months

Saturday 19th March 2022
quotequote all
For several years I've been using Microsoft Remote Desktop to control a server running WHS2011 from my iMac.

I've now bought a newer iMac, and am struggling to make a connection. The latest version of Remote Desktop doesn't seem to want to connect to the windows server, and the older version of Remote Desktop won't run on the latest version of osX.

Any suggestions?

AClownsPocket

899 posts

189 months

Saturday 19th March 2022
quotequote all
Download the trial version of Royal TS and give that a whirl.

xeny

5,498 posts

108 months

Saturday 19th March 2022
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FreeRDP is in macports.

jesusbuiltmycar

5,135 posts

284 months

Saturday 19th March 2022
quotequote all
I have been using MS Remote Desktop MacOS to connect to Windows (& Linux) for years … the issue is often incorrect configuration on the Windows end .

Can you still connect to the windows machine with your older Mac?

clockworks

Original Poster:

7,723 posts

175 months

Saturday 19th March 2022
quotequote all
jesusbuiltmycar said:
I have been using MS Remote Desktop MacOS to connect to Windows (& Linux) for years … the issue is often incorrect configuration on the Windows end .

Can you still connect to the windows machine with your older Mac?
I can't connect to it from the old iMac since I upgraded 2 days ago from Sierra to High Sierra in preparation to migrate everything to the new iMac. It was working fine before I did that. Nothing has changed on the Windows server.

clockworks

Original Poster:

7,723 posts

175 months

Saturday 19th March 2022
quotequote all
Exactly the same thing happens with Royal - as soon as the connection window starts up, it closes again.

CorradoTDI

1,835 posts

201 months

Saturday 19th March 2022
quotequote all
clockworks said:
Exactly the same thing happens with Royal - as soon as the connection window starts up, it closes again.
Probably something blocking the RDP port then...

clockworks

Original Poster:

7,723 posts

175 months

Saturday 19th March 2022
quotequote all
CorradoTDI said:
Probably something blocking the RDP port then...
That's beyond me. Any ideas where to start looking?

Just remembered I had a new BT router last week. Could it be something on that that's blocking the connection?

Does this port stuff apply if both machines are on the same local network?




Edited by clockworks on Saturday 19th March 21:53


Edited by clockworks on Saturday 19th March 22:05

clockworks

Original Poster:

7,723 posts

175 months

Saturday 19th March 2022
quotequote all
Maybe I'm getting something fundamentally wrong here?

When Microsoft Remote Desktop asks for "user account" and "password", are these the details that I would use to log onto the server if I was using its own screen and keyboard, or something else?


I'm trying to connect using the IP of the server.
Both machines are on my home network.
Firewall on the iMac is turned off.

jesusbuiltmycar

5,135 posts

284 months

Saturday 19th March 2022
quotequote all
With RDP

You enter the op address of the machine you are connecting to and use credentials for the machine you are connecting to …

So if your username on the Windows Machine is Clockwork and your username on the Mac is SomethingElse - use the credentials for Clockwork when connecting.

clockworks

Original Poster:

7,723 posts

175 months

Saturday 19th March 2022
quotequote all
jesusbuiltmycar said:
With RDP

You enter the op address of the machine you are connecting to and use credentials for the machine you are connecting to …

So if your username on the Windows Machine is Clockwork and your username on the Mac is SomethingElse - use the credentials for Clockwork when connecting.
That's what I've been trying, so it must be something else that's causing the problem.

jesusbuiltmycar

5,135 posts

284 months

Saturday 19th March 2022
quotequote all
clockworks said:
That's what I've been trying, so it must be something else that's causing the problem.
In that case it is a network config issue can you “ping” the windows px from the Mac?

Also can you “ping” the Mac from the windows PC?

clockworks

Original Poster:

7,723 posts

175 months

Saturday 19th March 2022
quotequote all
jesusbuiltmycar said:
In that case it is a network config issue can you “ping” the windows px from the Mac?

Also can you “ping” the Mac from the windows PC?
I'm not sure how to ping from the iMac?
The server is up in the loft, running headless.

I can see the server as a device on the iMac, and on the BT router's admin page.

I've just tried using Remote Desktop on my Android tablet, and I can't connect to the server from there either. Same thing - the window just closes again after a fraction of a second..

Could it be something set wrong on the router?

clockworks

Original Poster:

7,723 posts

175 months

Saturday 19th March 2022
quotequote all
OK, I tried pinging from the iMac - timeout.

I've got another server in the loft, which I used to use for music and video. I booted that one up, and I can connect to it using Remote Desktop. That proves that the iMac and network are OK.

There's something odd going on with the server that I'm having problems with.

Captain_Morgan

1,453 posts

89 months

Sunday 20th March 2022
quotequote all
Could it be ip related?

First and obvious Q have you confirmed the server is powered up?

How do you manage the server ip, dhcp? Dhcp reservations, static ip?

Perhaps the new router uses a different ip range and hence the server now has a different ip?

If static could the router have also assigned that ip via dhcp and you have a conflict?

Can you go onto the router and check your lease table to confirm if the server ip has been allocated?

Does your router let you ping devices if so what’s the result of pinging it from there?

Edit: rereading some of these q might be superfluous but it’s worth getting a base line.

Are the Mac and server bother wired connections?
Are there any other wired connections?

Once the ip is confirmed I’d see what a traceroute from the Mac to confirmed server op gives
If successful then I’d try ssh to the server and see what that does

I’d also try ping and traceroute to and from the Mac to other devices preferably trying a mix of wired and WiFi devices in case you have a a lack of connectivity between them (unlikely)

Edited by Captain_Morgan on Sunday 20th March 08:21

clockworks

Original Poster:

7,723 posts

175 months

Sunday 20th March 2022
quotequote all
Captain_Morgan said:
Could it be ip related?

First and obvious Q have you confirmed the server is powered up?

How do you manage the server ip, dhcp? Dhcp reservations, static ip?

Perhaps the new router uses a different ip range and hence the server now has a different ip?

If static could the router have also assigned that ip via dhcp and you have a conflict?

Can you go onto the router and check your lease table to confirm if the server ip has been allocated?

Does your router let you ping devices if so what’s the result of pinging it from there?

Edited by Captain_Morgan on Sunday 20th March 08:06
Server is powered up, activity lights flashing.

Static IP set on router

Router's admin page says server is connected, and it says "rdp" on the info page for the device. Presumably that means the router has seen activity on that port?

It's a BT smart hub, latest model. I can't see any option to ping from the router.

I've tried pinging the server from the iMac again this morning, and it now works.

Still no luck with making the connection with Remote Desktop though. I've deleted the device and added it again. If I use the wrong password, it comes back and tells me it failed. If I use the correct password, the window just closes in a fraction of a second. That suggest there is some communication going on?


colin79666

2,224 posts

143 months

Sunday 20th March 2022
quotequote all
Perhaps have a look in the event logs on the server, see if it has any pointers?

clockworks

Original Poster:

7,723 posts

175 months

Sunday 20th March 2022
quotequote all
colin79666 said:
Perhaps have a look in the event logs on the server, see if it has any pointers?
The issue is that it's running headless, and it's up in the loft.

Worst case, I'll have to get it down and plug it into a TV. I don't have an actual monitor anymore.

colin79666

2,224 posts

143 months

Sunday 20th March 2022
quotequote all
clockworks said:
The issue is that it's running headless, and it's up in the loft.

Worst case, I'll have to get it down and plug it into a TV. I don't have an actual monitor anymore.
Got an iPad? There is a Microsoft RDP app for that, might at least confirm if the same behaviour happens or if you do get in then can look at logs.

clockworks

Original Poster:

7,723 posts

175 months

Sunday 20th March 2022
quotequote all
Captain_Morgan said:
Could it be ip related?



Edit: rereading some of these q might be superfluous but it’s worth getting a base line.

Are the Mac and server bother wired connections?
Are there any other wired connections?

Once the ip is confirmed I’d see what a traceroute from the Mac to confirmed server op gives
If successful then I’d try ssh to the server and see what that does

I’d also try ping and traceroute to and from the Mac to other devices preferably trying a mix of wired and WiFi devices in case you have a a lack of connectivity between them (unlikely)

Edited by Captain_Morgan on Sunday 20th March 08:21
Server and iMac are on wired connections

Router is showing 29 wired connections.

Ping from iMac to server is working this morning.


I wonder if it's an issue with the Netgear managed switch? I'll go up into the loft shortly and try another port on the switch.