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SMB won't connect

After installing Monteray I can no longer connect my Synology NAS. When I try to log in it just "shakes" at the login window like it is the wrong login. It's the same login I use to connect from the browser to its Local IP address (which works fine) so I am wondering what I can check?

iMac 21.5″ 4K, macOS 10.15

Posted on Dec 31, 2021 6:07 AM

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Posted on Dec 31, 2021 4:33 PM

Kevinwal wrote:

Also, ask them if Monterey supports SMB 1, 2, or 3. If so where can it be enabled?

Additionally, does it support NTLMv1 Authentication or automatically use NTLMv2 Authentication?

I saw a few posts online that macOS still allows for SMB v1 connections to remote shares and this may be the problem. You can disable SMB v1 by using the instructions in this Apple article:

How to disable SMB 1 or NetBIOS in macOS - Apple Support


In theory I would expect the highest version to be used when negotiating with remote shares, but it seems this may not always be the case.

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Question marked as Best reply

Dec 31, 2021 4:33 PM in response to Kevinwal

Kevinwal wrote:

Also, ask them if Monterey supports SMB 1, 2, or 3. If so where can it be enabled?

Additionally, does it support NTLMv1 Authentication or automatically use NTLMv2 Authentication?

I saw a few posts online that macOS still allows for SMB v1 connections to remote shares and this may be the problem. You can disable SMB v1 by using the instructions in this Apple article:

How to disable SMB 1 or NetBIOS in macOS - Apple Support


In theory I would expect the highest version to be used when negotiating with remote shares, but it seems this may not always be the case.

Dec 31, 2021 1:49 PM in response to Kevinwal

Make sure the Caps Lock is not on. Try using an external keyboard (or another external keyboard if this is Desktop system).


It sounds like with Big Sur or earlier you were able to connect this Mac to the NAS and the only change was installing Monterey?


How are you trying to connect to the NAS? Are you using the Finder's "Go ---> Connect to Server ..." and using "smb://<ip-address-dns-name>/<share-name>"? Are you using the correct share name/share point?


Connecting to the NAS by browser or Finder may make a difference. Do you actually access files while logged in from a browser? or is that just an administrative interface for the NAS? An SMB share can have a completely different username and password from that used to administer a NAS.

Dec 31, 2021 2:33 PM in response to HWTech

Make sure the Caps Lock is not on. Try using an external keyboard (or another external keyboard if this is a Desktop system).

>>> caps lock is not on. Yes, this is an iMac but I also have tried to access it with Macbook. Same result


It sounds like with Big Sur or earlier you were able to connect this Mac to the NAS and the only change was installing Monterey?

>>> yes started with Monteray


How are you trying to connect to the NAS? Are you using the Finder's "Go ---> Connect to Server ..." and using "smb://<ip-address-dns-name>/<share-name>"? Are you using the correct share name/share point?

>>> Yes, using "Connect to Server" as I always have. Tried IP address and NAS Name as well.


Connecting to the NAS by browser or Finder may make a difference. Do you actually access files while logged in from a browser? or is that just an administrative interface for the NAS? An SMB share can have a completely different username and password from that used to administer a NAS.

>>> It is the admin interface but you can access files, which I have. I have tried access as Administrator and User as well.


Have had several exchanges with Synology who are quite sure what the issue is. The last exchange was:


"You may have to reach out to Apple Support for more assistance but can you check if you have Private Relay active in Monterey?


Also, ask them if Monterey supports SMB 1, 2, or 3. If so where can it be enabled?


Additionally, does it support NTLMv1 Authentication or automatically use NTLMv2 Authentication?


I've tried to check on "Private Relay" is definitely part of Monteray but it's also buggy and all I get is a "spinning wheel" when I tried to access it.


The last 2 questions I am not sure.


It feels like it's definitely a Monterey issue.


Thanks for taking the time to reply.


Jan 1, 2022 11:37 AM in response to Kevinwal

The instructions in the Apple article will create that file for you.


You can also do the same thing to a similar file located in your own home user folder's hidden Library folder ("~/Library/Preferences/nsmb.conf") which would only affect the one user instead of any user on that computer if you create the "/etc/nsmb.conf".



Jan 2, 2022 11:16 AM in response to Kevinwal

Kevinwal wrote:

Curiously, if I hadn't already mentioned. It will connect using AFP same credentials?

If the Synology is configured to share items with AFP, then Monterey should connect. I don't know how the Synology configures shares with various protocols; if there is one central user/password item it uses for each protocol configured (doubtful), or if you must manually configure the credentials for each type of share (SMB, AFP, NFS) with the latter being most likely.


Did you try rebooting the Mac after making the SMB changes?

Jan 3, 2022 5:55 AM in response to HWTech

I agree it should but it doesn't. I've had Synology involved as well even did a remote to check settings and everything is in order as far as they are concerned. There is only 1 password to sign on for SMB and AFP but 2 separate setting pages. Yes, when I made the SMB changes I rebooted. And as mentioned tried to also attach using a different computer.


Appears this will go down as one of those unsolvable things.

Jan 4, 2022 7:10 AM in response to Kevinwal

Unfortunately my technical knowledge of SMB shares is limited. During my quick search it appeared that this is not the first time Monterey (or even Big Sur) has had issues connecting to SMB shares. You will likely need to wait for another patch, unless another more knowledgeable contributor has some ideas.


You could try reporting the issue to Apple.


SMB won't connect

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