Hello Everybody Here is the infrastructure I want : Client => Internet => Squid => RDS Gateway => VM Here is my configuration : https_port public_name:443 accel cert=/etc/ssl/private/servercert.pem key=/etc/ssl/private/serverkey.pem cafile=/etc/ssl/private/intermediate.pem capath=/etc/ssl/private/ defaultsite=parentserver.domain.qh version=1 cache_peer parentservername parent 443 0 no-query originserver ssl sslcert=/etc/ssl/private/servercert.crt.pem sslkey=/etc/ssl/private/serverkey.pem sslcapath=/etc/ssl/private/ login=PASSTHRU connection-auth=on ssloptions=ALL name=gateway sslflags=DONT_VERIFY_PEER front-end-https=on no-digest acl RDS dstdomain parentservername cache_peer_access gateway allow all #cache_peer_access gateway deny all http_access allow all miss_access allow all #http_access allow RDS #http_access deny all #miss_access allow RDS #miss_access deny all debug_options ALL,2 # # Recommended minimum configuration: # # Example rule allowing access from your local networks. # Adapt to list your (internal) IP networks from where browsing # should be allowed acl localnet src 10.0.0.0/8 # RFC1918 possible internal network acl localnet src 172.16.0.0/12 # RFC1918 possible internal network acl localnet src 192.168.0.0/16 # RFC1918 possible internal network acl localnet src fc00::/7 # RFC 4193 local private network range acl localnet src fe80::/10 # RFC 4291 link-local (directly plugged) machines acl SSL_ports port 443 acl Safe_ports port 80 # http acl Safe_ports port 21 # ftp acl Safe_ports port 443 # https acl Safe_ports port 70 # gopher acl Safe_ports port 210 # wais acl Safe_ports port 1025-65535 # unregistered ports acl Safe_ports port 280 # http-mgmt acl Safe_ports port 488 # gss-http acl Safe_ports port 591 # filemaker acl Safe_ports port 777 # multiling http acl CONNECT method CONNECT # # Recommended minimum Access Permission configuration: # # Deny requests to certain unsafe ports http_access deny !Safe_ports # Deny CONNECT to other than secure SSL ports http_access deny CONNECT !SSL_ports # Only allow cachemgr access from localhost http_access allow localhost manager http_access deny manager cache_mem 8 MB # We strongly recommend the following be uncommented to protect innocent # web applications running on the proxy server who think the only # one who can access services on "localhost" is a local user #http_access deny to_localhost # # INSERT YOUR OWN RULE(S) HERE TO ALLOW ACCESS FROM YOUR CLIENTS # # Example rule allowing access from your local networks. # Adapt localnet in the ACL section to list your (internal) IP networks # from where browsing should be allowed http_access allow localnet http_access allow localhost # And finally deny all other access to this proxy http_access deny all # Uncomment and adjust the following to add a disk cache directory. cache_dir ufs /usr/local/squid/var/cache/squid 100 16 256 # Leave coredumps in the first cache dir #coredump_dir /usr/local/squid/var/cache/squid # # Add any of your own refresh_pattern entries above these. # refresh_pattern ^ftp: 1440 20% 10080 refresh_pattern ^gopher: 1440 0% 1440 refresh_pattern -i (/cgi-bin/|\?) 0 0% 0 refresh_pattern . 0 20% 4320 As you can see all is open but i have a problem. My configuration didn't work but yesterday I managed to log me 3 times from the office. Ten minutes after i could no longer log to the machine. I tried to log on at home last night and this morning and it worked. But now nobody can connect to the gateway. You can see the log when i could connect : 1372701961.331 79301 public_ip_client TCP_MISS_ABORTED/000 0 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip - 1372702018.639 8 public_ip_client TCP_MISS/401 695 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372702018.735 7 public_ip_client TCP_MISS/401 695 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372702025.441 6780 public_ip_client TCP_MISS_ABORTED/000 0 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip - 1372702025.441 6686 public_ip_client TCP_MISS_ABORTED/200 7319 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip application/rpc 1372702506.635 8 public_ip_client TCP_MISS/401 695 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372702506.728 7 public_ip_client TCP_MISS/401 695 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372702514.727 7963 public_ip_client TCP_MISS_ABORTED/200 103543 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip application/rpc 1372702514.728 8074 public_ip_client TCP_MISS_ABORTED/000 0 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip - 1372703139.182 11 public_ip_client TCP_MISS/401 695 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372703139.295 8 public_ip_client TCP_MISS/401 695 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372703146.054 6851 public_ip_client TCP_MISS_ABORTED/000 0 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip - 1372703146.054 6709 public_ip_client TCP_MISS_ABORTED/200 7319 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip application/rpc 1372706052.563 123 public_ip_client TCP_MISS/401 695 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372706052.687 7 public_ip_client TCP_MISS/401 695 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372706151.972 99259 public_ip_client TCP_MISS_ABORTED/200 14007 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip application/rpc 1372706151.972 99385 public_ip_client TCP_MISS_ABORTED/000 0 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip - 1372709339.193 118 public_ip_client TCP_MISS/401 695 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372709339.329 7 public_ip_client TCP_MISS/401 695 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372709383.530 44313 public_ip_client TCP_MISS_ABORTED/000 0 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip - 1372709383.532 44177 public_ip_client TCP_MISS/200 7319 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip application/rpc 1372710088.478 9 public_ip_client TCP_MISS/401 695 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372710088.584 7 public_ip_client TCP_MISS/401 695 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372710480.819 392320 public_ip_client TCP_MISS/502 4579 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip text/html 1372710480.819 392209 public_ip_client TCP_MISS/200 7231 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip application/rpc 1372744890.663 123 public_ip_client TCP_MISS/401 695 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372744890.772 7 public_ip_client TCP_MISS/401 695 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - FIRSTUP_PARENT/private_parentserver_ip text/plain 1372745699.263 808576 public_ip_client TCP_MISS/502 4583 RPC_IN_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip text/html 1372745699.263 808466 public_ip_client TCP_MISS/200 7371 RPC_OUT_DATA https://public_name.com/rpc/rpcproxy.dll? - PINNED/private_parentserver_ip application/rpc Even if I could connect you can see errors 401 and 502 The logs now : 1372768605.501 7 public_ip_client TCP_MISS/401 959 RDG_OUT_DATA https://public_name/remoteDesktopGateway/ - FIRSTUP_PARENT/private_parentserver_ip text/html 1372768605.663 1 public_ip_client TCP_MISS/502 4583 RDG_OUT_DATA https://public_name/remoteDesktopGateway/ - PINNED/private_parentserver_ip text/html 1372771702.991 17 public_ip_client TCP_MISS/401 959 RDG_OUT_DATA https://public_name/remoteDesktopGateway/ - FIRSTUP_PARENT/private_parentserver_ip text/html 1372771703.897 2 public_ip_client TCP_MISS/502 4561 RDG_OUT_DATA https://public_name/remoteDesktopGateway/ - PINNED/private_parentserver_ip text/html 1372771769.011 7 public_ip_client TCP_MISS/401 959 RDG_OUT_DATA https://public_name/remoteDesktopGateway/ - FIRSTUP_PARENT/private_parentserver_ip text/html 1372771769.466 2 public_ip_client TCP_MISS/502 4559 RDG_OUT_DATA https://public_name/remoteDesktopGateway/ - PINNED/private_parentserver_ip text/html 1372772425.281 7 public_ip_client TCP_MISS/401 959 RDG_OUT_DATA https://public_name/remoteDesktopGateway/ - FIRSTUP_PARENT/private_parentserver_ip text/html 1372772425.442 2 public_ip_client TCP_MISS/502 4573 RDG_OUT_DATA https://public_name/remoteDesktopGateway/ - PINNED/private_parentserver_ip text/html I'm confused, can you tell me if my setup looks good and if there is an explanation? 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