After 2 hours of testing I managed to create a workaround but wondering if anyone knows what the issue could be?
Running "apt update" I see these errors at the end of the process:
W: Failed to fetch http://ftp.debian.org/debian/dists/bookworm/InRelease Temporary failure resolving 'ftp.debian.org'
W: Failed to fetch http://ftp.debian.org/debian/dists/bookworm-updates/InRelease Temporary failure resolving 'ftp.debian.org'
W: Failed to fetch http://download.proxmox.com/debian/pve/dists/bookworm/InRelease Temporary failure resolving 'download.proxmox.com'
W: Failed to fetch http://security.debian.org/debian-security/dists/bookworm-security/InRelease Temporary failure resolving 'security.debian.org'
W: Some index files failed to download. They have been ignored, or old ones used instead.
Workaround:
1. modify
2. modify
Result:
Original Issue:
	
	
	
		
DNS tests to rule out general DNS/local network problems:
ftp.au.debian.org
				
			Running "apt update" I see these errors at the end of the process:
W: Failed to fetch http://ftp.debian.org/debian/dists/bookworm/InRelease Temporary failure resolving 'ftp.debian.org'
W: Failed to fetch http://ftp.debian.org/debian/dists/bookworm-updates/InRelease Temporary failure resolving 'ftp.debian.org'
W: Failed to fetch http://download.proxmox.com/debian/pve/dists/bookworm/InRelease Temporary failure resolving 'download.proxmox.com'
W: Failed to fetch http://security.debian.org/debian-security/dists/bookworm-security/InRelease Temporary failure resolving 'security.debian.org'
W: Some index files failed to download. They have been ignored, or old ones used instead.
Workaround:
1. modify
/etc/hosts127.0.0.1 localhost plex10.0.1.2 pve.internal pve103.76.41.50 download.proxmox.com151.101.2.132 deb.debian.org151.101.2.132 security.debian.org2. modify
/etc/apt/sources.list# Specific AU IP-based workaround testingdeb [URL]http://103.84.224.37/debian[/URL] bookworm main contribdeb [URL]http://103.84.224.37/debian[/URL] bookworm-updates main contribdeb [URL]http://security.debian.org/debian-security[/URL] bookworm-security main contribdeb [URL]http://download.proxmox.com/debian/pve[/URL] bookworm pve-no-subscriptionResult:
apt updateHit:1 [URL]http://103.84.224.37/debian[/URL] bookworm InReleaseHit:2 [URL]http://103.84.224.37/debian[/URL] bookworm-updates InReleaseHit:3 [URL]http://security.debian.org/debian-security[/URL] bookworm-security InReleaseHit:4 [URL]http://download.proxmox.com/debian/pve[/URL] bookworm InReleaseReading package lists... DoneBuilding dependency tree... DoneReading state information... DoneAll packages are up to date.Original Issue:
		Code:
	
	Linux pve 6.8.12-7-pve #1 SMP PREEMPT_DYNAMIC PMX 6.8.12-7 (2025-01-17T08:18Z) x86_64
Last login: Tue Mar 25 11:46:57 AEDT 2025 on pts/1
root@pve:~# sudo apt update
Ign:1 http://ftp.debian.org/debian bookworm InRelease
Ign:2 http://ftp.debian.org/debian bookworm-updates InRelease
Ign:3 http://download.proxmox.com/debian/pve bookworm InRelease
Ign:4 http://security.debian.org/debian-security bookworm-security InRelease
Ign:1 http://ftp.debian.org/debian bookworm InRelease
Ign:3 http://download.proxmox.com/debian/pve bookworm InRelease
Ign:2 http://ftp.debian.org/debian bookworm-updates InRelease
Ign:4 http://security.debian.org/debian-security bookworm-security InRelease
Ign:1 http://ftp.debian.org/debian bookworm InRelease
Ign:2 http://ftp.debian.org/debian bookworm-updates InRelease
Ign:3 http://download.proxmox.com/debian/pve bookworm InRelease
Ign:4 http://security.debian.org/debian-security bookworm-security InRelease
Ign:1 http://ftp.debian.org/debian bookworm InRelease
Ign:2 http://ftp.debian.org/debian bookworm-updates InRelease
Ign:3 http://download.proxmox.com/debian/pve bookworm InRelease
Ign:4 http://security.debian.org/debian-security bookworm-security InRelease
Ign:1 http://ftp.debian.org/debian bookworm InRelease
Ign:3 http://download.proxmox.com/debian/pve bookworm InRelease
Ign:2 http://ftp.debian.org/debian bookworm-updates InRelease
Ign:4 http://security.debian.org/debian-security bookworm-security InRelease
Err:3 http://download.proxmox.com/debian/pve bookworm InRelease
  Temporary failure resolving 'download.proxmox.com'
Err:1 http://ftp.debian.org/debian bookworm InRelease
  Temporary failure resolving 'ftp.debian.org'
Err:2 http://ftp.debian.org/debian bookworm-updates InRelease
  Temporary failure resolving 'ftp.debian.org'
Err:4 http://security.debian.org/debian-security bookworm-security InRelease
  Temporary failure resolving 'security.debian.org'
Reading package lists... Done
Building dependency tree... Done
Reading state information... Done
All packages are up to date.
W: Failed to fetch http://ftp.debian.org/debian/dists/bookworm/InRelease  Temporary failure resolving 'ftp.debian.org'
W: Failed to fetch http://ftp.debian.org/debian/dists/bookworm-updates/InRelease  Temporary failure resolving 'ftp.debian.org'
W: Failed to fetch http://download.proxmox.com/debian/pve/dists/bookworm/InRelease  Temporary failure resolving 'download.proxmox.com'
W: Failed to fetch http://security.debian.org/debian-security/dists/bookworm-security/InRelease  Temporary failure resolving 'security.debian.org'
W: Some index files failed to download. They have been ignored, or old ones used instead.DNS tests to rule out general DNS/local network problems:
- nslookup Tests:- Ran nslookup download.proxmox.com 8.8.8.8, resolved to 103.76.41.50.
- Ran nslookup deb.debian.org 8.8.8.8 and nslookup security.debian.org 8.8.8.8, resolved to IPs like 151.101.2.132.
- Confirmed system DNS servers (8.8.8.8, 1.1.1.1 from /etc/resolv.conf) work for these domains.
 
- Ping Tests:- Ran ping download.proxmox.com, succeeded with responses, showing network reachability.
- Similar results for deb.debian.org and security.debian.org, ruling out connectivity issues.
 
- Curl Tests:- Ran curl -I http://download.proxmox.com/debian/pve/, returned "HTTP/1.1 200 OK".
- Confirmed network can reach servers, suggesting no local network blockages.
 
- Checked DNS Configuration:- Ran cat /etc/resolv.conf, showed nameserver 8.8.8.8 and nameserver 1.1.1.1, verifying correct DNS settings.
 
- Network Path Verification:- Ran traceroute to domains, showed hops through pfSense (10.0.1.1) with no local blockages.
- Ran ping 8.8.8.8, confirmed low latency and no packet loss to DNS servers.
 
- Apt-Specific Debugging:- Ran strace -f -e trace=network apt update 2>&1 | grep -E "(8.8.8.8|1.1.1.1|resolv)", showed DNS queries failing with "Temporary failure resolving", despite system-wide success.
 
- IP Workaround:- Used http://103.84.224.37/debian in /etc/apt/sources.list for ftp.au.debian.org, worked for that repo, but CDN-based ones like security.debian.org failed without /etc/hosts.
 
ftp.au.debian.org
- Resolution Status (Apt, Without /etc/hosts): Fails to resolve
- Resolution Status (Apt, With /etc/hosts): Resolves with IP in sources.list
- Resolution Status (Other Tools): Resolves successfully
- Notes: Worked when using IP (103.84.224.37) directly in /etc/apt/sources.list.
- Resolution Status (Apt, Without /etc/hosts): Fails to resolve
- Resolution Status (Apt, With /etc/hosts): Resolves with /etc/hosts
- Resolution Status (Other Tools): Resolves successfully
- Notes: CDN-based with dynamic IPs, resolution fails without /etc/hosts entry (e.g., 151.101.2.132).
- Resolution Status (Apt, Without /etc/hosts): Fails to resolve
- Resolution Status (Apt, With /etc/hosts): Resolves with /etc/hosts
- Resolution Status (Other Tools): Resolves successfully
- Notes: CDN-based, similar DNS issue to deb.debian.org, requires hostname or /etc/hosts entry (e.g., 151.101.2.132).
- Resolution Status (Apt, Without /etc/hosts): Fails to resolve
- Resolution Status (Apt, With /etc/hosts): Resolves with /etc/hosts
- Resolution Status (Other Tools): Resolves successfully
- Notes: Static IP (103.76.41.50), works with hostname when resolved via /etc/hosts.
			
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