Cloudflared Service isn't starting on Ubuntu after update

Zero Trust Cloudflare Tunnel
1

I updated the Cloudflare daemon installed on my Ubuntu machine (Jammy) today. Immediately after the update, the cloudflared tunnel went inactive and isn’t able to establish QUIC connection anymore.

I see the following logs on my installed service:

Mar 01 21:10:11 alexandrium cloudflared[61095]: 2024-03-02T02:10:11Z INF Retrying connection in up to 1m4s connIndex=0 event=0 ip=198.41.200.193
Mar 01 21:10:43 alexandrium cloudflared[61095]: 2024-03-02T02:10:43Z ERR Unable to establish connection with Cloudflare edge error="DialContext error: dial tcp 198.41.192.47:7844: i/o timeout" connIndex=0 event=0 ip=198.41.192.47
Mar 01 21:10:43 alexandrium cloudflared[61095]: 2024-03-02T02:10:43Z ERR Serve tunnel error error="DialContext error: dial tcp 198.41.192.47:7844: i/o timeout" connIndex=0 event=0 ip=198.41.192.47
Mar 01 21:10:43 alexandrium cloudflared[61095]: 2024-03-02T02:10:43Z INF Retrying connection in up to 1m4s connIndex=0 event=0 ip=198.41.192.47
Mar 01 21:11:00 alexandrium cloudflared[61095]: 2024-03-02T02:11:00Z ERR Unable to establish connection with Cloudflare edge error="DialContext error: dial tcp 198.41.200.193:7844: i/o timeout" connIndex=0 event=0 ip=198.41.200.193
Mar 01 21:11:00 alexandrium cloudflared[61095]: 2024-03-02T02:11:00Z ERR Serve tunnel error error="DialContext error: dial tcp 198.41.200.193:7844: i/o timeout" connIndex=0 event=0 ip=198.41.200.193
Mar 01 21:11:00 alexandrium cloudflared[61095]: 2024-03-02T02:11:00Z INF Retrying connection in up to 1m4s connIndex=0 event=0 ip=198.41.200.193
Mar 01 21:11:22 alexandrium cloudflared[61095]: 2024-03-02T02:11:22Z ERR Unable to establish connection with Cloudflare edge error="DialContext error: dial tcp 198.41.200.233:7844: i/o timeout" connIndex=0 event=0 ip=198.41.200.233
Mar 01 21:11:22 alexandrium cloudflared[61095]: 2024-03-02T02:11:22Z ERR Serve tunnel error error="DialContext error: dial tcp 198.41.200.233:7844: i/o timeout" connIndex=0 event=0 ip=198.41.200.233
Mar 01 21:11:22 alexandrium cloudflared[61095]: 2024-03-02T02:11:22Z INF Retrying connection in up to 1m4s connIndex=0 event=0 ip=198.41.200.233
Mar 01 21:11:48 alexandrium cloudflared[61095]: 2024-03-02T02:11:48Z ERR Unable to establish connection with Cloudflare edge error="DialContext error: dial tcp 198.41.200.193:7844: i/o timeout" connIndex=0 event=0 ip=198.41.200.193
Mar 01 21:11:48 alexandrium cloudflared[61095]: 2024-03-02T02:11:48Z ERR Serve tunnel error error="DialContext error: dial tcp 198.41.200.193:7844: i/o timeout" connIndex=0 event=0 ip=198.41.200.193
Mar 01 21:11:48 alexandrium cloudflared[61095]: 2024-03-02T02:11:48Z INF Retrying connection in up to 1m4s connIndex=0 event=0 ip=198.41.200.193
Mar 01 21:12:34 alexandrium cloudflared[61095]: 2024-03-02T02:12:34Z ERR Unable to establish connection with Cloudflare edge error="DialContext error: dial tcp 198.41.192.47:7844: i/o timeout" connIndex=0 event=0 ip=198.41.192.47
Mar 01 21:12:34 alexandrium cloudflared[61095]: 2024-03-02T02:12:34Z ERR Serve tunnel error error="DialContext error: dial tcp 198.41.192.47:7844: i/o timeout" connIndex=0 event=0 ip=198.41.192.47
Mar 01 21:12:34 alexandrium cloudflared[61095]: 2024-03-02T02:12:34Z INF Retrying connection in up to 1m4s connIndex=0 event=0 ip=198.41.192.47

i tried reinstalling the service and kickstarting new tunnels. nothing would give!

3

That error means it was unable to reach the IP. Is your machine about to reach those IPs normally?

4

Yes. The IP were all accessible otherwise, as there isn’t a firewall issue because I went down that path. I restarted the machine, and it connected correctly later on—so I’m not sure what was breaking. This machine uses Wi-Fi6 to connect with the Verizon router, and I suspect an issue there.

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