I'm afraid the 1.2.19 in xenial-proposed does not seem to solve the problem here: estan@newton:~$ apt-cache policy apt apt: Installerad: 1.2.19 Kandidat: 1.2.19 Versionstabell: *** 1.2.19 500 500 http://archive.ubuntu.com/ubuntu xenial-proposed/main amd64 Packages 100 /var/lib/dpkg/status 1.2.18 500 500 http://se.archive.ubuntu.com/ubuntu xenial-updates/main amd64 Packages 1.2.15ubuntu0.2 500 500 http://security.ubuntu.com/ubuntu xenial-security/main amd64 Packages 1.2.10ubuntu1 500 500 http://se.archive.ubuntu.com/ubuntu xenial/main amd64 Packages estan@newton:~$ /usr/lib/apt/apt-helper download-file http://downloads.sourceforge.net/corefonts/andale32.exe test.exe Fel:1 http://downloads.sourceforge.net/corefonts/andale32.exe 404 Not Found E: Misslyckades med att hämta https://vorboss.dl.sourceforge.net/project/corefonts/the fonts/final/andale32.exe 404 Not Found E: Hämtning misslyckades estan@newton:~$ wget http://downloads.sourceforge.net/corefonts/andale32.exe --2017-01-18 19:10:15-- http://downloads.sourceforge.net/corefonts/andale32.exe Slår upp downloads.sourceforge.net (downloads.sourceforge.net)... 216.34.181.59 Ansluter till downloads.sourceforge.net (downloads.sourceforge.net)|216.34.181.59|:80... ansluten. HTTP-begäran skickad, väntar på svar... 301 Moved Permanently Adress: http://downloads.sourceforge.net/project/corefonts/the%20fonts/final/andale32.exe [följer] --2017-01-18 19:10:15-- http://downloads.sourceforge.net/project/corefonts/the%20fonts/final/andale32.exe Ansluter till downloads.sourceforge.net (downloads.sourceforge.net)|216.34.181.59|:80... ansluten. HTTP-begäran skickad, väntar på svar... 302 Found Adress: https://netcologne.dl.sourceforge.net/project/corefonts/the%20fonts/final/andale32.exe [följer] --2017-01-18 19:10:16-- https://netcologne.dl.sourceforge.net/project/corefonts/the%20fonts/final/andale32.exe Slår upp netcologne.dl.sourceforge.net (netcologne.dl.sourceforge.net)... 78.35.24.46, 2001:4dd0:1234:6::5f Ansluter till netcologne.dl.sourceforge.net (netcologne.dl.sourceforge.net)|78.35.24.46|:443... ansluten. HTTP-begäran skickad, väntar på svar... 200 OK Längd: 198384 (194K) [application/octet-stream] Sparar till: "andale32.exe" andale32.exe 100%[========================================================================================================================================>] 193,73K 1,25MB/s in 0,2s 2017-01-18 19:10:16 (1,25 MB/s) - "andale32.exe" sparades [198384/198384] estan@newton:~$ cat /etc/lsb-release DISTRIB_ID=Ubuntu DISTRIB_RELEASE=16.04 DISTRIB_CODENAME=xenial DISTRIB_DESCRIPTION="Ubuntu 16.04.1 LTS" estan@newton:~$ And I'm afraid it's not deterministic; this is the output from three runs: estan@newton:~$ /usr/lib/apt/apt-helper download-file http://downloads.sourceforge.net/corefonts/andale32.exe test.exe Fel:1 http://downloads.sourceforge.net/corefonts/andale32.exe 404 Not Found E: Misslyckades med att hämta https://netix.dl.sourceforge.net/project/corefonts/the fonts/final/andale32.exe 404 Not Found E: Hämtning misslyckades estan@newton:~$ /usr/lib/apt/apt-helper download-file http://downloads.sourceforge.net/corefonts/andale32.exe test.exe Fel:1 http://downloads.sourceforge.net/corefonts/andale32.exe 404 Not Found E: Misslyckades med att hämta https://netix.dl.sourceforge.net/project/corefonts/the fonts/final/andale32.exe 404 Not Found E: Hämtning misslyckades estan@newton:~$ /usr/lib/apt/apt-helper download-file http://downloads.sourceforge.net/corefonts/andale32.exe test.exe Läs:1 http://downloads.sourceforge.net/corefonts/andale32.exe [198 kB] Hämtade 198 kB på 1s (142 kB/s) estan@newton:~$ The two first ones failed while the last one succeeded. Here's the output with -o debug::acquire::https=1 -o debug::acquire::http=1 for a successful run: estan@newton:~$ /usr/lib/apt/apt-helper -o debug::acquire::https=1 -o debug::acquire::http=1 download-file http://downloads.sourceforge.net/corefonts/andale32.exe test.exe 0% [Arbetar]GET /corefonts/andale32.exe HTTP/1.1 Host: downloads.sourceforge.net User-Agent: Debian APT-HTTP/1.3 (1.2.19) Answer for: http://downloads.sourceforge.net/corefonts/andale32.exe HTTP/1.1 301 Moved Permanently Server: nginx Date: Wed, 18 Jan 2017 18:13:17 GMT Content-Type: text/html; charset=UTF-8 Connection: close Location: http://downloads.sourceforge.net/project/corefonts/the%20fonts/final/andale32.exe Content-Length: 178 0% [Arbetar]GET /project/corefonts/the%20fonts/final/andale32.exe HTTP/1.1 Host: downloads.sourceforge.net User-Agent: Debian APT-HTTP/1.3 (1.2.19) GET /project/corefonts/the%20fonts/final/andale32.exe HTTP/1.1 Host: downloads.sourceforge.net User-Agent: Debian APT-HTTP/1.3 (1.2.19) Answer for: http://downloads.sourceforge.net/project/corefonts/the fonts/final/andale32.exe HTTP/1.1 302 Found Server: nginx Date: Wed, 18 Jan 2017 18:13:18 GMT Content-Type: text/html; charset=UTF-8 Connection: close content-disposition: attachment; filename="andale32.exe" Set-Cookie: sf_mirror_attempt="corefonts:netassist:the%20fonts/final/andale32.exe"; expires=120; Path=/ Location: https://netassist.dl.sourceforge.net/project/corefonts/the%20fonts/final/andale32.exe Content-Length: 165 0% [Arbetar]* Trying 62.205.134.42... * Connected to netassist.dl.sourceforge.net (62.205.134.42) port 443 (#0) * found 174 certificates in /etc/ssl/certs/ca-certificates.crt * found 708 certificates in /etc/ssl/certs * ALPN, offering http/1.1 0% [Arbetar]* SSL connection using TLS1.2 / ECDHE_RSA_AES_256_GCM_SHA384 * server certificate verification OK * server certificate status verification SKIPPED * common name: netassist.dl.sourceforge.net (matched) * server certificate expiration date OK * server certificate activation date OK * certificate public key: RSA * certificate version: #3 * subject: CN=netassist.dl.sourceforge.net * start date: Thu, 05 Jan 2017 23:28:00 GMT * expire date: Wed, 05 Apr 2017 23:28:00 GMT * issuer: C=US,O=Let's Encrypt,CN=Let's Encrypt Authority X3 * compression: NULL * ALPN, server did not agree to a protocol > GET /project/corefonts/the fonts/final/andale32.exe HTTP/1.1 Host: netassist.dl.sourceforge.net User-Agent: Debian APT-CURL/1.0 (1.2.15) Accept: */* Cache-Control: max-age=0 0% [Arbetar]< HTTP/1.1 200 OK < Server: nginx < Date: Wed, 18 Jan 2017 18:32:55 GMT < Content-Type: application/octet-stream < Content-Length: 198384 < Last-Modified: Thu, 15 Aug 2002 14:33:49 GMT < Connection: close < ETag: "3d5bbbcd-306f0" < Accept-Ranges: bytes < Läs:1 http://downloads.sourceforge.net/corefonts/andale32.exe [198 kB] 53% [1 test.exe 131 kB/198 kB 66%]* Closing connection 0 Hämtade 198 kB på 16s (12,0 kB/s) estan@newton:~$ And here's for a failed run: estan@newton:~$ /usr/lib/apt/apt-helper -o debug::acquire::https=1 -o debug::acquire::http=1 download-file http://downloads.sourceforge.net/corefonts/andale32.exe test.exe 0% [Arbetar]GET /corefonts/andale32.exe HTTP/1.1 Host: downloads.sourceforge.net Range: bytes=198384- If-Range: Thu, 15 Aug 2002 14:33:49 GMT User-Agent: Debian APT-HTTP/1.3 (1.2.19) Answer for: http://downloads.sourceforge.net/corefonts/andale32.exe HTTP/1.1 301 Moved Permanently Server: nginx Date: Wed, 18 Jan 2017 18:17:19 GMT Content-Type: text/html; charset=UTF-8 Connection: close Location: http://downloads.sourceforge.net/project/corefonts/the%20fonts/final/andale32.exe Content-Length: 178 0% [Arbetar]GET /project/corefonts/the%20fonts/final/andale32.exe HTTP/1.1 Host: downloads.sourceforge.net Range: bytes=198384- If-Range: Thu, 15 Aug 2002 14:33:49 GMT User-Agent: Debian APT-HTTP/1.3 (1.2.19) GET /project/corefonts/the%20fonts/final/andale32.exe HTTP/1.1 Host: downloads.sourceforge.net Range: bytes=198384- If-Range: Thu, 15 Aug 2002 14:33:49 GMT User-Agent: Debian APT-HTTP/1.3 (1.2.19) Answer for: http://downloads.sourceforge.net/project/corefonts/the fonts/final/andale32.exe HTTP/1.1 302 Found Server: nginx Date: Wed, 18 Jan 2017 18:17:20 GMT Content-Type: text/html; charset=UTF-8 Connection: close content-disposition: attachment; filename="andale32.exe" Set-Cookie: sf_mirror_attempt="corefonts:freefr:the%20fonts/final/andale32.exe"; expires=120; Path=/ Location: https://freefr.dl.sourceforge.net/project/corefonts/the%20fonts/final/andale32.exe Content-Length: 162 0% [Arbetar]* Trying 88.191.250.136... * Connected to freefr.dl.sourceforge.net (88.191.250.136) port 443 (#0) * found 174 certificates in /etc/ssl/certs/ca-certificates.crt * found 708 certificates in /etc/ssl/certs * ALPN, offering http/1.1 0% [Arbetar]* SSL connection using TLS1.2 / ECDHE_RSA_AES_256_GCM_SHA384 * server certificate verification OK * server certificate status verification SKIPPED * common name: freefr.dl.sourceforge.net (matched) * server certificate expiration date OK * server certificate activation date OK * certificate public key: RSA * certificate version: #3 * subject: CN=freefr.dl.sourceforge.net * start date: Fri, 30 Dec 2016 23:34:00 GMT * expire date: Thu, 30 Mar 2017 23:34:00 GMT * issuer: C=US,O=Let's Encrypt,CN=Let's Encrypt Authority X3 * compression: NULL * ALPN, server accepted to use http/1.1 > GET /project/corefonts/the fonts/final/andale32.exe HTTP/1.1 Host: freefr.dl.sourceforge.net User-Agent: Debian APT-CURL/1.0 (1.2.15) Accept: */* Cache-Control: max-age=0 Range: bytes=198384- If-Range: Thu, 15 Aug 2002 14:33:49 GMT 0% [Arbetar]< HTTP/1.1 302 Found < Date: Wed, 18 Jan 2017 18:17:20 GMT < Server: Apache < Location: https://downloads.sourceforge.net/project/corefonts/the?download&failedmirror=freefr.dl.sourceforge.net < Content-Length: 291 < Connection: close < Content-Type: text/html; charset=iso-8859-1 < * Closing connection 0 * Issue another request to this URL: 'https://downloads.sourceforge.net/project/corefonts/the?download&failedmirror=freefr.dl.sourceforge.net' * Trying 216.34.181.59... * Connected to downloads.sourceforge.net (216.34.181.59) port 443 (#1) * found 174 certificates in /etc/ssl/certs/ca-certificates.crt * found 708 certificates in /etc/ssl/certs * ALPN, offering http/1.1 0% [Arbetar]* SSL connection using TLS1.2 / ECDHE_RSA_AES_256_CBC_SHA1 * server certificate verification OK * server certificate status verification SKIPPED * common name: *.sourceforge.net (matched) * server certificate expiration date OK * server certificate activation date OK * certificate public key: RSA * certificate version: #3 * subject: C=US,ST=California,L=San Diego,O=SourceForge Media\, LLC,OU=sourceforge.net,CN=*.sourceforge.net * start date: Tue, 13 Dec 2016 00:00:00 GMT * expire date: Fri, 12 Jan 2018 23:59:59 GMT * issuer: C=US,O=GeoTrust Inc.,CN=GeoTrust SSL CA - G3 * compression: NULL * ALPN, server did not agree to a protocol > GET /project/corefonts/the?download&failedmirror=freefr.dl.sourceforge.net HTTP/1.1 Host: downloads.sourceforge.net User-Agent: Debian APT-CURL/1.0 (1.2.15) Accept: */* Cache-Control: max-age=0 Range: bytes=198384- If-Range: Thu, 15 Aug 2002 14:33:49 GMT < HTTP/1.1 404 Not Found < Server: nginx < Date: Wed, 18 Jan 2017 18:17:22 GMT < Content-Type: text/html; charset=UTF-8 < Connection: close < Content-Length: 154 < * Closing connection 1 Fel:1 http://downloads.sourceforge.net/corefonts/andale32.exe 404 Not Found E: Misslyckades med att hämta https://freefr.dl.sourceforge.net/project/corefonts/the fonts/final/andale32.exe 404 Not Found E: Hämtning misslyckades estan@newton:~$