Something changed between 0.4.1 and 0.5.0

[roadkingvrod]

Describe the Bug

I noticed that I couldn't connect recently and that there were changes in the server and client so I did some testing.

Server 1.14.1 works with client 0.4.1

Server 1.15.1 works with client 0.5.0

Server 1.15.1 does not work with 0.5.0. - Sits on "Registering" and never leaves or turns orange.

Standard windows 11 machine (same machine for all tests). The only thing I see in the docker logs that stands out with the failed connections is.

2026-01-25T17:34:45+00:00 [info]: Handling register olm message!
2026-01-25T17:34:45+00:00 [warn]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-25T17:34:46+00:00 [info]: Handling register olm message!
2026-01-25T17:34:46+00:00 [warn]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-25T17:34:47+00:00 [info]: Handling register olm message!
2026-01-25T17:34:47+00:00 [warn]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-25T17:34:48+00:00 [info]: Handling register olm message!
2026-01-25T17:34:48+00:00 [warn]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-25T17:34:48+00:00 [info]: All connections removed for OLM ID: xxxx
2026-01-25T17:34:48+00:00 [info]: Client disconnected - OLM ID: xxxx
2026-01-25T17:35:23+00:00 [info]: Establishing websocket connection
2026-01-25T17:35:23+00:00 [info]: Client added to tracking - OLM ID: xxxx, Connection ID: xxxxxecxxx2xxx2-xxx-xxxxx, Total connections: 1, Config version: 0
2026-01-25T17:35:23+00:00 [info]: WebSocket connection fully established and ready - OLM ID: xxxx
2026-01-25T17:35:23+00:00 [info]: Handling register olm message!
2026-01-25T17:35:24+00:00 [info]: Public key mismatch. Updating public key and clearing session info...
2026-01-25T17:35:24+00:00 [warn]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-25T17:35:24+00:00 [info]: Handling register olm message!
2026-01-25T17:35:24+00:00 [warn]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-25T17:35:25+00:00 [info]: Handling register olm message!
2026-01-25T17:35:26+00:00 [warn]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-25T17:35:26+00:00 [info]: Handling register olm message!
2026-01-25T17:35:26+00:00 [warn]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-25T17:35:27+00:00 [info]: All connections removed for OLM ID: xxxxx

Happy to do more testing if I can assist.

Environment

See Above.

To Reproduce

Connect as usual

Expected Behavior

connects the same as the old versions.

[earetaurus]

yep 5.0.0 doesn't work for me either 0.4.1 works fine something broke

[oschwartz10612]

Hum... I am unable to replicate. Could you provide the logs from the windows app when it is attempting to connect but failing in the registering state? You can go to more > preferences > logs and connect and then save the logs. Also please make sure UDP port 21820 is open on the VPS and you are on the latest Gerbil version 1.3.0 and UDP port 21820 is in the docker compose.

[miloschwartz]

Can you check the Windows client logs to see what it's trying to do as it fails? Provide as much context as possible, but redact an sensitive info. You can check logs at Pangolin > More > Preferences > Logs

[roadkingvrod]

Here you go. If i redacted too much, please let me know as I did anything that looked like at token.

INFO: 2026/01/26 15:12:48 Pangolin logging initialized - log file: C:\ProgramData\Pangolin\logs\pangolin.log, log level: debug
INFO: 2026/01/26 15:12:48 Pangolin version 0.5.0 starting
INFO: 2026/01/26 15:12:48 Cannot access service manager without admin privileges
INFO: 2026/01/26 15:12:48 Attempting to install/start manager service (will show UAC prompt)...
INFO: 2026/01/26 15:12:48 Elevate: ShellExecute called - program: C:\Program Files\Pangolin\Pangolin.exe, args: /installmanagerservice
INFO: 2026/01/26 15:12:50 Elevate: ShellExecute succeeded
INFO: 2026/01/26 15:12:50 Pangolin logging initialized - log file: C:\ProgramData\Pangolin\logs\pangolin.log, log level: debug
INFO: 2026/01/26 15:12:50 Pangolin version 0.5.0 starting
INFO: 2026/01/26 15:12:50 Pangolin logging initialized - log file: C:\ProgramData\Pangolin\logs\pangolin.log, log level: debug
INFO: 2026/01/26 15:12:50 Pangolin version 0.5.0 starting
INFO: 2026/01/26 15:12:50 Starting as manager service
INFO: 2026/01/26 15:12:50 Manager service installed successfully
INFO: 2026/01/26 15:12:50 Pangolin Manager service starting
INFO: 2026/01/26 15:12:50 Starting UI process for user 'struc@streetglide' for session 2
INFO: 2026/01/26 15:12:50 Updater: CheckForUpdate() called
INFO: 2026/01/26 15:12:50 Updater: checkForUpdate() started (keepSession=false)
INFO: 2026/01/26 15:12:50 Updater: Current version: 0.5.0, Architecture: amd64
INFO: 2026/01/26 15:12:50 Updater: Creating WinHTTP session with User-Agent: pangolin-windows-0.5.0
INFO: 2026/01/26 15:12:50 Pangolin logging initialized - log file: C:\ProgramData\Pangolin\logs\pangolin.log, log level: debug
INFO: 2026/01/26 15:12:50 Pangolin version 0.5.0 starting
INFO: 2026/01/26 15:12:50 Connected to manager service via IPC
INFO: 2026/01/26 15:12:50 Updater: WinHTTP session created successfully
INFO: 2026/01/26 15:12:50 Updater: Connecting to update server: static.pangolin.net:443 (HTTPS=true)
INFO: 2026/01/26 15:12:50 Updater: Connected to update server successfully
INFO: 2026/01/26 15:12:50 Updater: Fetching manifest from: /windows-client/latest.sig
INFO: 2026/01/26 15:12:50 APIClient initialized with baseURL: https://pangolin.sitename.com
INFO: 2026/01/26 15:12:50 Making request to: https://pangolin.sitename.com/api/v1/
INFO: 2026/01/26 15:12:50 Updater: Manifest response received
INFO: 2026/01/26 15:12:50 Updater: Read 318 bytes from manifest
INFO: 2026/01/26 15:12:50 Updater: Parsing manifest file list
INFO: 2026/01/26 15:12:50 Updater: Parsing signed file list (input size: 318 bytes)
INFO: 2026/01/26 15:12:50 Updater: Decoding public key from base64
INFO: 2026/01/26 15:12:50 Updater: Public key decoded successfully (length: 42)
INFO: 2026/01/26 15:12:50 Updater: Manifest has 3 lines as expected
INFO: 2026/01/26 15:12:50 Updater: Untrusted comment found: untrusted comment: verify with release.pub
INFO: 2026/01/26 15:12:50 Updater: Decoding signature from base64
INFO: 2026/01/26 15:12:50 Updater: Signature decoded (length: 74)
INFO: 2026/01/26 15:12:50 Updater: Signature format valid, verifying...
INFO: 2026/01/26 15:12:50 Updater: ✓ Ed25519 signature verified successfully
INFO: 2026/01/26 15:12:50 Updater: Parsing 2 file hash lines
INFO: 2026/01/26 15:12:50 Updater: Parsed file entry: pangolin-amd64-0.5.0.msi (hash: 32989cb0e72952f4df3d9ee124d76a58cc3b6084c834c76be55877dd87b5ade2, location: https://github.com/fosrl/windows/releases/download/0.5.0/pangolin-amd64-0.5.0.msi)
INFO: 2026/01/26 15:12:50 Updater: Skipping empty last line
INFO: 2026/01/26 15:12:50 Updater: Successfully parsed 1 file entries from manifest
INFO: 2026/01/26 15:12:50 Updater: Manifest parsed successfully, found 1 files
INFO: 2026/01/26 15:12:50 Updater: Searching for update candidate
INFO: 2026/01/26 15:12:50 Updater: findCandidate() - Current version: 0.5.0, Architecture: amd64
INFO: 2026/01/26 15:12:50 Updater: Looking for files matching prefix: pangolin-amd64-, suffix: .msi
INFO: 2026/01/26 15:12:50 Updater: Total files in manifest: 1
INFO: 2026/01/26 15:12:50 Updater: Manifest contains file: pangolin-amd64-0.5.0.msi
INFO: 2026/01/26 15:12:50 Updater: Checking file: pangolin-amd64-0.5.0.msi
INFO: 2026/01/26 15:12:50 Updater: File pangolin-amd64-0.5.0.msi - hasPrefix(pangolin-amd64-): true, hasSuffix(.msi): true
INFO: 2026/01/26 15:12:50 Updater: File matches pattern! Extracted version: 0.5.0
INFO: 2026/01/26 15:12:50 Updater: Comparing candidate version 0.5.0 with current version 0.5.0
INFO: 2026/01/26 15:12:50 Updater: Comparing versions - candidate: 0.5.0, current: 0.5.0
INFO: 2026/01/26 15:12:50 Updater: Candidate parts: [0 5 0], Current parts: [0 5 0]
INFO: 2026/01/26 15:12:50 Updater: Comparing 3 version components
INFO: 2026/01/26 15:12:50 Updater: Component 0 - candidate: 0, current: 0
INFO: 2026/01/26 15:12:50 Updater: Component 0 matches, continuing
INFO: 2026/01/26 15:12:50 Updater: Component 1 - candidate: 5, current: 5
INFO: 2026/01/26 15:12:50 Updater: Component 1 matches, continuing
INFO: 2026/01/26 15:12:50 Updater: Component 2 - candidate: 0, current: 0
INFO: 2026/01/26 15:12:50 Updater: Component 2 matches, continuing
INFO: 2026/01/26 15:12:50 Updater: All components match - candidate is not newer
INFO: 2026/01/26 15:12:50 Updater: Version comparison result - 0.5.0 is newer than 0.5.0: false
INFO: 2026/01/26 15:12:50 Updater: Candidate version 0.5.0 is not newer, skipping
INFO: 2026/01/26 15:12:50 Updater: No update candidate found after checking all 1 files
INFO: 2026/01/26 15:12:50 Updater: No update candidate found
INFO: 2026/01/26 15:12:50 Updater: Closing connection
INFO: 2026/01/26 15:12:50 Updater: Closing WinHTTP session
INFO: 2026/01/26 15:12:50 Updater: CheckForUpdate completed - no update found
INFO: 2026/01/26 15:12:50 Making request to: https://pangolin.sitename.com/api/v1/user
INFO: 2026/01/26 15:12:50 Making request to: https://pangolin.sitename.com/api/v1/user/0fwpbylkmv7pwfy/orgs
INFO: 2026/01/26 15:12:50 Making request to: https://pangolin.sitename.com/api/v1/server-info
INFO: 2026/01/26 15:12:50 Connected to manager service - update checking handled by manager
INFO: 2026/01/26 15:12:52 Making request to: https://pangolin.sitename.com/api/v1/
INFO: 2026/01/26 15:12:52 Making request to: https://pangolin.sitename.com/api/v1/user
INFO: 2026/01/26 15:12:52 Making request to: https://pangolin.sitename.com/api/v1/user/0fwpbylkmv7pwfy/orgs
INFO: 2026/01/26 15:12:52 Organizations refreshed successfully: 1 orgs
INFO: 2026/01/26 15:12:53 Making request to: https://pangolin.sitename.com/api/v1/user/0fwpbylkmv7pwfy/olm/ir4o1yqepbrwljb
INFO: 2026/01/26 15:12:53 OLM credentials verified successfully
INFO: 2026/01/26 15:12:53 Connecting tunnel with config: Name=olm, Endpoint=https://pangolin.sitename.com
INFO: 2026/01/26 15:12:53 Tunnel: StartTunnel called
INFO: 2026/01/26 15:12:53 Tunnel: Starting tunnel with config
INFO: 2026/01/26 15:12:53 Tunnel state changed: registering
INFO: 2026/01/26 15:12:53 Pangolin logging initialized - log file: C:\ProgramData\Pangolin\logs\pangolin.log, log level: debug
INFO: 2026/01/26 15:12:53 Pangolin version 0.5.0 starting
INFO: 2026/01/26 15:12:53 Starting as tunnel service with config: C:\ProgramData\Pangolin\Tunnels\olm.json
INFO: 2026/01/26 15:12:53 Tunnel service: Starting with config
INFO: 2026/01/26 15:12:53 Tunnel service: Running as Windows service
INFO: 2026/01/26 15:12:53 Tunnel service: Service starting
INFO: 2026/01/26 15:12:53 Starting status polling
INFO: 2026/01/26 15:12:53 Started OLM status polling (every 1 second)
DEBUG: 2026/01/26 15:12:53 Build tunnel called: config: {Name:olm Endpoint:https://pangolin.sitename.com ID:ir4o1yqepbrwljb Secret:v16qbqf683669gumdkwnbtsc8ybgx7l4vho3ylu76sg7ret2 MTU:1280 DNS:9.9.9.9 Holepunch:true PingIntervalSeconds:5 PingTimeoutSeconds:5 UserToken:XXXXXXXXXXXXXXXXXXX OrgID:thome InterfaceName:Pangolin UpstreamDNS:[9.9.9.9:53] OverrideDNS:true TunnelDNS:false}
DEBUG: 2026/01/26 15:12:53 Checking permissions for native interface
INFO: 2026/01/26 15:12:53 Tunnel state changed: registering
DEBUG: 2026/01/26 15:12:53 Posture check: Antivirus - Executing PowerShell command: Get-CimInstance -Namespace 'root/SecurityCenter2' -ClassName AntiVirusProduct | Select-Object -ExpandProperty productState
DEBUG: 2026/01/26 15:12:53 Posture check: Disk Encryption - Executing PowerShell command: Get-BitLockerVolume -MountPoint 'C:' | Select-Object -ExpandProperty VolumeStatus
DEBUG: 2026/01/26 15:12:53 Posture check: Firewall - Executing PowerShell command: (Get-NetFirewallProfile | Where-Object { $.Enabled -eq $true }).Count -gt 0
DEBUG: 2026/01/26 15:12:53 Posture check: Disk Encryption - Command failed with error: exec: "powershell.exe": executable file not found in %PATH%
DEBUG: 2026/01/26 15:12:53 Posture check: Antivirus - Command failed with error: exec: "powershell.exe": executable file not found in %PATH%
DEBUG: 2026/01/26 15:12:53 Posture check: TPM - Executing PowerShell command: Get-Tpm | Select-Object -ExpandProperty TpmPresent
DEBUG: 2026/01/26 15:12:53 Posture check: Firewall - Command failed with error: exec: "powershell.exe": executable file not found in %PATH%
DEBUG: 2026/01/26 15:12:53 Posture check: TPM - Command failed with error: exec: "powershell.exe": executable file not found in %PATH%
DEBUG: 2026/01/26 15:12:53 Created named pipe at \.\pipe\pangolin-olm with write access for everyone
INFO: 2026/01/26 15:12:53 Starting HTTP server on socket \.\pipe\pangolin-olm
INFO: 2026/01/26 15:12:53 Starting OLM tunnel...
DEBUG: 2026/01/26 15:12:53 Build tunnel completed successfully
DEBUG: 2026/01/26 15:12:53 Starting tunnel with config: {Endpoint:https://pangolin.sitename.com ID:ir4o1yqepbrwljb Secret:XXXXXXXXXXXXXXXXXXXXXXXX UserToken:XXXXXXXXXXXXXXXXXXXXXXX MTU:1280 DNS:9.9.9.9 UpstreamDNS:[9.9.9.9:53] InterfaceName:Pangolin Holepunch:true TlsClientCert: PingIntervalDuration:5s PingTimeoutDuration:5s OrgID:thome FileDescriptorTun:0 FileDescriptorUAPI:0 EnableUAPI:false OverrideDNS:true TunnelDNS:false InitialFingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:XXXXXXXXXXXXXXXXXXX serialNumber: username:WORKGROUP\STREETGLIDE$] InitialPostures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] DisableRelay:false}
DEBUG: 2026/01/26 15:12:53 Posture check: Antivirus - Executing PowerShell command: Get-CimInstance -Namespace 'root/SecurityCenter2' -ClassName AntiVirusProduct | Select-Object -ExpandProperty productState
DEBUG: 2026/01/26 15:12:53 Posture check: Disk Encryption - Executing PowerShell command: Get-BitLockerVolume -MountPoint 'C:' | Select-Object -ExpandProperty VolumeStatus
DEBUG: 2026/01/26 15:12:53 Posture check: Firewall - Executing PowerShell command: (Get-NetFirewallProfile | Where-Object { $.Enabled -eq $true }).Count -gt 0
DEBUG: 2026/01/26 15:12:53 Posture check: Antivirus - Command failed with error: exec: "powershell.exe": executable file not found in %PATH%
DEBUG: 2026/01/26 15:12:53 Posture check: TPM - Executing PowerShell command: Get-Tpm | Select-Object -ExpandProperty TpmPresent
DEBUG: 2026/01/26 15:12:53 Posture check: Disk Encryption - Command failed with error: exec: "powershell.exe": executable file not found in %PATH%
INFO: 2026/01/26 15:12:53 Created shared UDP socket on port 54689 (refcount: 2)
DEBUG: 2026/01/26 15:12:53 Posture check: Firewall - Command failed with error: exec: "powershell.exe": executable file not found in %PATH%
DEBUG: 2026/01/26 15:12:53 Posture check: TPM - Command failed with error: exec: "powershell.exe": executable file not found in %PATH%
DEBUG: 2026/01/26 15:12:53 websocket: Requesting token from https://pangolin.sitename.com/api/v1/auth/olm/get-token with body: {"olmId":"X","orgId":"thome","secret":"XXXXXXX"}
DEBUG: 2026/01/26 15:12:54 websocket: Received token: XXXXXXXX
DEBUG: 2026/01/26 15:12:54 Got exit nodes for hole punching: [{pangolin.sitename.com 21820 k+xXXXXXX+XXXXXX= [15 16 13]}]
DEBUG: 2026/01/26 15:12:54 Updated hole punch exit nodes: [{pangolin.sitename.com 21820 k+xxxxxxx/XXXXXX+bpnSpggKQtf4XVvZD4gOfC8= [15 16 13]}]
INFO: 2026/01/26 15:12:54 Starting hole punch for 1 exit nodes
DEBUG: 2026/01/26 15:12:54 Starting UDP hole punch to 1 exit nodes with shared bind
DEBUG: 2026/01/26 15:12:54 Resolved exit node: pangolin.sitename.com -> XXXXXX:21820
DEBUG: 2026/01/26 15:12:54 Sent UDP hole punch to XXXXXXX:21820: {"ephemeralPublicKey":"XXXXXXX/XXXXXX=","nonce":"XXXXXX+Qv","ciphertext":"XXXXXXX+XXXXXXX+XXXXXXX/tpsOK/KXB6FIq/V0VFI1AxSCAlRw=="}
INFO: 2026/01/26 15:12:54 Websocket Connected
DEBUG: 2026/01/26 15:12:54 Sending registration message to server with public key: XXXXXXX= and relay: false
INFO: 2026/01/26 15:12:54 Tunnel: OLM registered
DEBUG: 2026/01/26 15:12:54 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:XXXXXXX serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:XXXXXXX= relay:false userToken:XXXXXXX]
DEBUG: 2026/01/26 15:12:55 Sent UDP hole punch to xx254.98.xxx:21820: {"ephemeralPublicKey":"XXXXXXX=","nonce":"XXXXXX+XXXXXX","ciphertext":"XXXXX"
DEBUG: 2026/01/26 15:12:55 Increased hole punch interval to 2s
DEBUG: 2026/01/26 15:12:55 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
DEBUG: 2026/01/26 15:12:56 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
DEBUG: 2026/01/26 15:12:57 Sent UDP hole punch to xx254.98.xxx:21820: {"ephemeralPublicKey":"VTRxTAQM7xF9fzJ5UM9diG/yscfzw1vOcJ7/SEsTXyg=","nonce":"mWEi/geDCgxWq4uN","ciphertext":"IjqmFa4+1YKQBCviIdAv267v3xqdmmVw73NqeBLBVDp/0MoDkv3DMoF0VDwhMaid3P/XXXXXXX/7+XXXXXXX+XXXXXXXXXXXXXXXXXX=="}
DEBUG: 2026/01/26 15:12:57 Increased hole punch interval to 4s
DEBUG: 2026/01/26 15:12:57 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
DEBUG: 2026/01/26 15:12:58 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
DEBUG: 2026/01/26 15:12:59 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
DEBUG: 2026/01/26 15:13:00 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
DEBUG: 2026/01/26 15:13:01 Sent UDP hole punch to xx254.98.xxx:21820: {"ephemeralPublicKey":"4mR64w2txHkLsCyjbObPbGWFW4OIBlaqnTgrbew7phM=","nonce":"VmNj+xxxxxxxxxxxx+6","ciphertext":"PycOAO++aVpPM4+lcoD1HNdW7ucccWKVvbMNuUT6eSPtzPwitGfC/XXXXXXXXXXXXXXXXXXXXXXXXXXXXXX/hMSyXXXXXXXXXXXXXXX5kUyeUSbykORriTfMIA=="}
DEBUG: 2026/01/26 15:13:01 Increased hole punch interval to 8s
DEBUG: 2026/01/26 15:13:01 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
DEBUG: 2026/01/26 15:13:02 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
DEBUG: 2026/01/26 15:13:03 websocket: Sending message: olm/wg/register, data: map[fingerprint:map[arch:amd64 deviceModel:XPS 9320 hostname:streetglide kernelVersion:Windows 10 0 Build 26200 osVersion:Windows 10 0 Build 26200 platform:windows platformFingerprint:xxxxxxxxx serialNumber: username:WORKGROUP\STREETGLIDE$] olmAgent:Pangolin Windows olmVersion:0.5.0 orgId:thome postures:map[diskEncrypted:false firewallEnabled:false tpmAvailable:false windowsAntivirusEnabled:false] publicKey:xxxxxxxxx= relay:false userToken:xxxxxxxxx]
INFO: 2026/01/26 15:13:04 websocket: SendMessageInterval timed out after 10 attempts for message type: olm/wg/register
DEBUG: 2026/01/26 15:13:09 Sent UDP hole punch to xx254.98.xxx:21820: {"ephemeralPublicKey":"XXXXXXXXXXXXXXXX+hhGaIUUUXXXXXXXXXXXXXXXXvOAw=","nonce":"a5XXXXXXXvNJ","ciphertext":"rxxxxxxxNUUT4sIH7mY1/xHzgdsxzxxxxxx7ikTFvU+zCxxxxxa72HkV9hDtuWt7u1cdzesSScIdy0QT82C/XXxxxxCJSwHtg=="}
DEBUG: 2026/01/26 15:13:09 Increased hole punch interval to 16s
INFO: 2026/01/26 15:13:19 Making request to: https://pangolin.sitename.com/api/v1/
INFO: 2026/01/26 15:13:19 Making request to: https://pangolin.sitename.com/api/v1/user
INFO: 2026/01/26 15:13:19 Making request to: https://pangolin.sitename.com/api/v1/user/0fwpbylkmv7pwfy/orgs
INFO: 2026/01/26 15:13:19 Organizations refreshed successfully: 1 orgs
INFO: 2026/01/26 15:13:20 Quit requested with stopTunnelsOnQuit=true, stopping all tunnels
INFO: 2026/01/26 15:13:20 Stopping tunnel: olm
INFO: 2026/01/26 15:13:20 Tunnel service: Service stopping
DEBUG: 2026/01/26 15:13:20 Destroy tunnel called
INFO: 2026/01/26 15:13:20 Stopping api server
INFO: 2026/01/26 15:13:20 All tunnels stopped
INFO: 2026/01/26 15:13:20 Manager service quit requested
DEBUG: 2026/01/26 15:13:20 Named pipe \.\pipe\pangolin-olm will be automatically cleaned up
INFO: 2026/01/26 15:13:20 Stopping tunnel process
INFO: 2026/01/26 15:13:20 Tunnel process context cancelled, cleaning up
DEBUG: 2026/01/26 15:13:20 websocket: connection closed during shutdown
INFO: 2026/01/26 15:13:20 OLM tunnel stopped
INFO: 2026/01/26 15:13:20 Exited UI process for user 'struc@streetglide' for session 2 with status 0
DEBUG: 2026/01/26 15:13:20 websocket: Sending message: olm/disconnecting, data: map[]
DEBUG: 2026/01/26 15:13:20 No DNS configurator to restore
INFO: 2026/01/26 15:13:20 Hole punch manager stopped
DEBUG: 2026/01/26 15:13:20 Releasing shared bind (refcount before release: 2)
INFO: 2026/01/26 15:13:20 Released shared UDP bind
INFO: 2026/01/26 15:13:20 Olm service stopped
INFO: 2026/01/26 15:13:20 Cleared all network settings
INFO: 2026/01/26 15:13:20 Tunnel process stopped
DEBUG: 2026/01/26 15:13:20 Destroy tunnel completed successfully
DEBUG: 2026/01/26 15:13:20 Hole punch stopped by signal
INFO: 2026/01/26 15:13:20 UDP hole punch goroutine ended for all exit nodes

[miloschwartz]

Aside from the failure to fingerprint and posture check, it seems like the requests to register are failing over and over.

Is it still showing failed to hole punch on the server? Do you see anything else in the server logs? Perhaps did you ever archive the device (there was a bug that would break the client if archived on previous versions)? Are you able to connect to Pangolin Cloud (trying to figure out if this is server specific or client specific)?

One thing you could try is to delete the client server side so it gets recreated: https://docs.pangolin.net/self-host/advanced/container-cli-tool#delete-client

[roadkingvrod]

It still shows the holepunch error on the server. Nothing else on the server logs related whatsoever. I did not archive the device, and as I mentioned, if i uninstall and install 0.4.1, it works flawlessly on the same machine (no reboot or anything). If I let it upgrade, it immediately fails on the first connect. I haven't used cloud, so I'll have to figure out what to do there.

I'll fire up a vm and install fresh, but based on the version issues, I don't expect much luck.

[roadkingvrod]

Ok, I upgraded to 0.5.1 and tested again.

Cloud seems to connect fine. I don't have anything configured there, but it did connect and give the orange icon.

On self hosted, I deleted the clients using the CLI and re set up my user. It did not connect. Interesting note though is that on the server under clients, it now shows 2 user devices (only tested on one). On the main screen, it shows one of them with the correct client version 0.5.1, but the other shows nothing under client version. Looking deeper, they also have different client id's. I suspect some of the issue could be tied to that? I'll also paste the entire server log below. I stopped all services and then started again so they would be clean for the test:

More info: When I went to delete the 2 clients that showed up again, one did not have an OLM associated:

Deleting client with orgId: thome, niceId: easy-going-plains-pocket-gopher...
Found client with clientId: 12
Found 0 OLM(s) associated with this client
Deleted 0 current fingerprint(s)
Deleted 0 OLM(s)
Deleted 0 approval(s)

Deleted 1 userClient association(s)
Deleted client: Windows Laptop

Client deletion completed successfully!

Summary:

• Client: easy-going-plains-pocket-gopher (clientId: 12)
• Olm(s): 0
• Current fingerprints: deleted
• Approvals: deleted
• UserClients: deleted
• Snapshots: preserved (not deleted)
  /app #
  /app # pangctl delete-client --orgId "thome" --niceId "distorted-german-cockroach"
  Deleting client with orgId: thome, niceId: distorted-german-cockroach...
  Found client with clientId: 13
  Found 1 OLM(s) associated with this client
  Deleted 1 current fingerprint(s)
  Deleted 1 OLM(s)
  Deleted 0 approval(s)
  Deleted 1 userClient association(s)
  Deleted client: Windows Laptop

Client deletion completed successfully!

Summary:

• Client: distorted-german-cockroach (clientId: 13)
• Olm(s): 1
• Current fingerprints: deleted
• Approvals: deleted
• UserClients: deleted
• Snapshots: preserved (not deleted)

One more update: I also get stuck on registering using the android client. Perhaps something legacy from being a long time user of pangolin?

Next step is I'll wipe the config and install fresh with all current versions and see if it works then.

@fosrl/pangolin@0.0.0 start
ENVIRONMENT=prod node dist/migrations.mjs && ENVIRONMENT=prod NODE_ENV=development node --enable-source-maps dist/server.mjs

Starting migrations from version 1.15.0
Migrations to run:
All migrations completed successfully
2026-01-28T16:11:12+00:00 [�[32minfo�[39m]: Pangolin gathers anonymous usage data to help us better understand how the software is used and guide future improvements and feature development. You can find more details, including instructions for opting out of this anonymous data collection, at: https://docs.pangolin.net/telemetry
2026-01-28T16:11:12+00:00 [�[32minfo�[39m]: API server is running on http://localhost:3000
2026-01-28T16:11:12+00:00 [�[32minfo�[39m]: Internal server is running on http://localhost:3001
2026-01-28T16:11:13+00:00 [�[32minfo�[39m]: Next.js server is running on http://localhost:3002
2026-01-28T16:11:18+00:00 [�[32minfo�[39m]: Updated exit node reachableAt to http://gerbil:3003
2026-01-28T16:11:24+00:00 [�[32minfo�[39m]: Establishing websocket connection
2026-01-28T16:11:24+00:00 [�[32minfo�[39m]: Client added to tracking - NEWT ID: xxxx, Connection ID: xxxxx, Total connections: 1, Config version: 0
2026-01-28T16:11:24+00:00 [�[32minfo�[39m]: WebSocket connection fully established and ready - NEWT ID: xxxxxx
2026-01-28T16:11:24+00:00 [�[32minfo�[39m]: Establishing websocket connection
2026-01-28T16:11:24+00:00 [�[32minfo�[39m]: Client added to tracking - NEWT ID: xxxxx, Connection ID: xxxx, Total connections: 1, Config version: 0
2026-01-28T16:11:24+00:00 [�[32minfo�[39m]: WebSocket connection fully established and ready - NEWT ID: xxxxx
2026-01-28T16:11:26+00:00 [�[32minfo�[39m]: Establishing websocket connection
2026-01-28T16:11:26+00:00 [�[32minfo�[39m]: Client added to tracking - NEWT ID: xxxx, Connection ID: xxxx, Total connections: 1, Config version: 0
2026-01-28T16:11:26+00:00 [�[32minfo�[39m]: WebSocket connection fully established and ready - NEWT ID: xxxx
2026-01-28T16:11:34+00:00 [�[32minfo�[39m]: Establishing websocket connection
2026-01-28T16:11:34+00:00 [�[32minfo�[39m]: Client added to tracking - OLM ID: xxxxx, Connection ID: xxxx Total connections: 1, Config version: 0
2026-01-28T16:11:34+00:00 [�[32minfo�[39m]: WebSocket connection fully established and ready - OLM ID: xxxxx
2026-01-28T16:11:35+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:35+00:00 [�[32minfo�[39m]: Public key mismatch. Updating public key and clearing session info...
2026-01-28T16:11:35+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:35+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:36+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:36+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:37+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:37+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:38+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:38+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:39+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:39+00:00 [�[32minfo�[39m]: Handling ping request newt message!
2026-01-28T16:11:39+00:00 [�[32minfo�[39m]: Sticking with previously connected node: Exit Node k+ZSfMf0 (0 ms), latency diff = 0.0ms / NaN%.
2026-01-28T16:11:39+00:00 [�[32minfo�[39m]: Adding peer with public key xxxxxx/xxxx= to exit node 1
2026-01-28T16:11:39+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:40+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:40+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:41+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:41+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:42+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:42+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:43+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:11:43+00:00 [�[32minfo�[39m]: Handling register olm message!
2026-01-28T16:11:44+00:00 [�[33mwarn�[39m]: Client last hole punch is too old and we have sites to send; skipping this register
2026-01-28T16:12:03+00:00 [�[32minfo�[39m]: All connections removed for OLM ID: xxxxx
xxxx

[roadkingvrod]

Ok, final update as it seems I need to move this to either newt or the server.

After significant back and forth trial and error, it seems I know where the conflict is. It appears to break when I have sites configured with newt. If i have no newt sites configured, i can connect with no problem. If i have a newt site configured it doesn't work.

The interesting thing is that the newt sites do function, however I have noticed this in their status:

INFO: 2026/01/28 16:03:01 Tunnel connection to server established successfully!
INFO: 2026/01/28 16:03:21 SendMessageInterval timed out after 10 attempts for message type: newt/wg/get-config

I assume it's like related. But short answer, it seems more focused on newt/server than on the client (though it's odd that 0.4.1 still works) Thanks!

[roadkingvrod]

Final final update. :)

I solved it. Ultmately it's tied back to me having used pangoiin since the early days and not staying up to date on the current documentation. I didn't open port 21820 on my firewall, only 51820.

So ultimately a user fail. I'm sorry about that, and thank you for investigating.