Hello, I realized I did not cover all angles in my last log. In this iteration I am forcing Lighttpd to set Last-Modified headers for files without extensions, with all no-cache settings from previous case removed on both sides.
Here is what Release returns now: $ curl -I https://deb.domain.com/dists/squeeze/Release HTTP/1.1 200 OK Content-Type: application/octet-stream Accept-Ranges: bytes ETag: "1447745436" Last-Modified: Thu, 05 Apr 2012 20:41:42 GMT Content-Length: 3036 Date: Thu, 05 Apr 2012 23:30:45 GMT With APT receiving a 416: * About to connect() to deb.domain.com port 443 (#0) * Trying 111.111.111.111... * connected * Connected to deb.domain.com (111.111.111.111) port 443 (#0) * found 141 certificates in /etc/ssl/certs/ca-certificates.crt * SSL re-using session ID * server certificate verification OK * common name: *.domain.com (matched) * server certificate expiration date OK * server certificate activation date OK * certificate public key: RSA * certificate version: #3 * subject: serialNumber=ad6c57sfKqXkXIhW0z7vi8OkT/Z62ORi,C=US,ST=NewYork,L=NewYork,O=Domain Inc\, Inc.,OU=SSL Services,CN=*.domain.com * start date: Wed, 15 Feb 2012 15:54:10 GMT * expire date: Tue, 19 Mar 2013 00:17:25 GMT * issuer: C=US,O=GeoTrust\, Inc.,CN=GeoTrust SSL CA * compression: NULL * cipher: AES-128-CBC * MAC: SHA1 > GET /dists/squeeze/Release HTTP/1.1 User-Agent: 1_99dbb35850fbb8668f2a3b27a6d97c75ab0bb58d Host: deb.domain.com Accept: */* Cache-Control: max-age=0 Range: bytes=63739- If-Range: Thu, 05 Apr 2012 20:41:42 GMT * The requested URL returned error: 416 * Closing connection #0 -- To UNSUBSCRIBE, email to [email protected] with a subject of "unsubscribe". Trouble? Contact [email protected]

