I did not do anything special outside of the steps in my repro to
specifically enable SSL in the nginx configs, but should that matter in
terms of running these SSL tests? With the Dockerfile in the description
as it is, I can already see in the test output that SSL tests are
running and succeeding with libssl1.1 on version 1.1.0g-2ubuntu4.3 and
failing on version 1.1.1-1ubuntu2.1~18.04.2.

Here is one example (mail_ssl.t):

Dockerfile with libssl1.1=1.1.0g-2ubuntu4.3:
www-data@8c157d70f8a2:/nginx-tests$ prove mail_ssl.t
mail_ssl.t..ok
All tests successful.
Files=1, Tests=22,  0 wallclock secs ( 0.02 usr  0.00 sys +  0.15 cusr  0.27 
csys =  0.44 CPU)
Result: PASS

Dockerfile with libssl1.1=1.1.1-1ubuntu2.1~18.04.2:
www-data@2a68517d6b29:/nginx-tests$ prove mail_ssl.t 
mail_ssl.t .. 140319190012352:error:2406F079:random number 
generator:RAND_load_file:Cannot open 
file:../crypto/rand/randfile.c:88:Filename=/var/www/.rnd   
140531605090752:error:2406F079:random number generator:RAND_load_file:Cannot 
open file:../crypto/rand/randfile.c:88:Filename=/var/www/.rnd   
mail_ssl.t .. 1/22       
#   Failed test 'builtin session reused'    
#   at mail_ssl.t line 187.       
#          got: '0'        
#     expected: '1'        
           
#   Failed test 'builtin size session reused'    
#   at mail_ssl.t line 199.       
#          got: '0'        
#     expected: '1'        
           
#   Failed test 'shared session reused'    
#   at mail_ssl.t line 205.       
#          got: '0'        
#     expected: '1'        
# Looks like you failed 3 tests of 22.        
mail_ssl.t .. Dubious, test returned 3 (wstat 768, 0x300)     
Failed 3/22 subtests   
           
Test Summary Report     
-------------------                                                             
                                                                                
             _ssl.t (Wstat: 768 Tests: 22 Failed: 3)         
  Failed tests:  3, 5-6        
  Non-zero exit status: 3          
Files=1, Tests=22,  1 wallclock secs ( 0.02 usr  0.01 sys +  0.16 cusr  0.25 
csys =  0.44 CPU)       
Result: FAIL

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https://bugs.launchpad.net/bugs/1833476

Title:
  libssl1.1 version 1.1.1-1ubuntu2.1~18.04.2 breaks nginx ssl tests

Status in nginx package in Ubuntu:
  Incomplete
Status in openssl package in Ubuntu:
  New

Bug description:
  Many nginx ssl tests pass with libssl1.1 version 1.1.0g-2ubuntu4.3 but
  fail when libssl1.1 is updated to version 1.1.1-1ubuntu2.1~18.04.2.

  Repro steps:
  1. Create control Dockerfile:
  ==========================================
  FROM ubuntu:18.04

  RUN apt-get update -y && \
    apt-get upgrade -y && \
    apt-get install -y git nginx-core xdg-utils openssl=1.1.0g-2ubuntu4.3 
libnet-ssleay-perl=1.84-1build1 libio-socket-ssl-perl=2.056-1 
libssl1.1=1.1.0g-2ubuntu4.3

  RUN git clone https://github.com/nginx/nginx-tests.git
  WORKDIR /nginx-tests

  ENV TEST_NGINX_BINARY=/usr/sbin/nginx
  ENV TEST_NGINX_MODULES=/usr/lib/nginx/modules

  USER www-data

  ENTRYPOINT ["prove", "."]
  ==========================================

  2. Run the command in a directory with only the Dockerfile:
  docker build -t nginx_image . && docker run --rm -it nginx_image

  3. See output:
  ==========================================
  Test Summary Report
  -------------------
  ./grpc_request_buffering.t               (Wstat: 512 Tests: 14 Failed: 2)
    Failed tests:  11-12
    Non-zero exit status: 2
  ./h2_server_tokens.t                     (Wstat: 1536 Tests: 14 Failed: 6)
    Failed tests:  1-2, 7-8, 10-11
    Non-zero exit status: 6
  ./upstream_ip_hash_ipv6.t                (Wstat: 512 Tests: 0 Failed: 0)
    Non-zero exit status: 2
    Parse errors: No plan found in TAP output
  Files=346, Tests=3782, 317 wallclock secs ( 1.87 usr  0.78 sys + 35.84 cusr 
16.99 csys = 55.48 CPU)                                                         
                
  Result: FAIL
  ==========================================

  4. Create new Dockerfile (only difference is updating libssl1.1):
  ==========================================
  FROM ubuntu:18.04

  RUN apt-get update -y && \
    apt-get upgrade -y && \
    apt-get install -y git nginx-core xdg-utils openssl=1.1.0g-2ubuntu4.3 
libnet-ssleay-perl=1.84-1build1 libio-socket-ssl-perl=2.056-1 
libssl1.1=1.1.1-1ubuntu2.1~18.04.2

  RUN git clone https://github.com/nginx/nginx-tests.git
  WORKDIR /nginx-tests

  ENV TEST_NGINX_BINARY=/usr/sbin/nginx
  ENV TEST_NGINX_MODULES=/usr/lib/nginx/modules

  USER www-data

  ENTRYPOINT ["prove", "."]
  ==========================================

  5. See output
  ==========================================
  Test Summary Report
  -------------------
  ./grpc_request_buffering.t               (Wstat: 512 Tests: 14 Failed: 2)
    Failed tests:  11-12
    Non-zero exit status: 2
  ./h2_server_tokens.t                     (Wstat: 1536 Tests: 14 Failed: 6)
    Failed tests:  1-2, 7-8, 10-11
    Non-zero exit status: 6
  ./mail_ssl.t                             (Wstat: 768 Tests: 22 Failed: 3)
    Failed tests:  3, 5-6
    Non-zero exit status: 3
  ./proxy_ssl.t                            (Wstat: 512 Tests: 9 Failed: 2)
    Failed tests:  4-5
    Non-zero exit status: 2
  ./stream_proxy_ssl.t                     (Wstat: 512 Tests: 8 Failed: 2)
    Failed tests:  4-5
    Non-zero exit status: 2
  ./stream_ssl.t                           (Wstat: 768 Tests: 9 Failed: 3)
    Failed tests:  2, 4-5
    Non-zero exit status: 3
  ./stream_upstream_zone_ssl.t             (Wstat: 768 Tests: 11 Failed: 3)
    Failed tests:  4-5, 9
    Non-zero exit status: 3
  ./upstream_ip_hash_ipv6.t                (Wstat: 512 Tests: 0 Failed: 0)
    Non-zero exit status: 2
    Parse errors: No plan found in TAP output
  ./upstream_zone_ssl.t                    (Wstat: 768 Tests: 11 Failed: 3)
    Failed tests:  4-5, 9
    Non-zero exit status: 3
  Files=346, Tests=3764, 317 wallclock secs ( 2.00 usr  0.73 sys + 36.49 cusr 
16.91 csys = 56.13 CPU)
  Result: FAIL
  ==========================================

  New failures: mail_ssl.t, proxy_ssl.t, stream_proxy_ssl.t,
  stream_ssl.t, stream_upstream_zone_ssl.t, upstream_zone_ssl.t.

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