Merge ~lucaskanashiro/ubuntu/+source/ruby-net-ssh:jammy-fix-openssl-3 into ubuntu/+source/ruby-net-ssh:ubuntu/jammy-devel

[Lucas Kanashiro]

Fix OpenSSL 3 issues in Jammy (LP: #1964025). This was fixed in version 1:7.0.0~beta1-2 in kinetic, and now I am backporting the upstream patch set to fix it in Jammy. This issue is making vagrant unusable, and some user are complaining about it.

PPA with proposed package:

https://launchpad.net/~lucaskanashiro/+archive/ubuntu/openssl3/+packages

autopkgtest result:

autopkgtest [19:06:49]: @@@@@@@@@@@@@@@@@@@@ summary
gem2deb-test-runner PASS

[Utkarsh Gupta (utkarsh)]

review: Approve

[Utkarsh Gupta (utkarsh)]

Well,

 ruby-net-ssh | 1:6.1.0-2 | jammy/universe | source, all
 ruby-net-ssh | 1:6.1.0-2 | kinetic/universe | source, all
 ruby-net-ssh | 1:7.0.0~beta1-2 | kinetic-proposed/universe | source, all

Hopefully 7.0.0~beta1-2 will migrate soon otherwise version in Jammy will be greater than in Kinetic.

[Lucas Kanashiro (lucaskanashiro)]

So far there is no regression because of new ruby-net-ssh in kinetic, and I do not expect any TBH. It did not migrate yet because of the long test queue we have at the moment, so I am not worried about it.

[Lucas Kanashiro (lucaskanashiro)]

However, since you mentioned the version string, I think I'll use 1:6.1.0-3ubuntu0.1 instead of 1:6.1.0-3ubuntu1. Thanks for making me revisit this :)

[Lucas Kanashiro (lucaskanashiro)]

Package uploaded:

Uploading ruby-net-ssh_6.1.0-3ubuntu0.1.dsc
Uploading ruby-net-ssh_6.1.0-3ubuntu0.1.debian.tar.xz
Uploading ruby-net-ssh_6.1.0-3ubuntu0.1_source.changes

Unmerged commits

8257009... by Lucas Kanashiro on 2022-05-09

update-maintainer

81cb3cd... by Lucas Kanashiro on 2022-05-09

Update changelog

1c25ff2... by Lucas Kanashiro on 2022-05-09

d/ruby-tests.rake: use custom openssl config file if using openssl 3

This will allow the usage of legacy ciphers during tests, not breaking a
bunch of them.

2108453... by Lucas Kanashiro on 2022-05-09

Backport upstream patches to support OpenSSL 3 (LP: #1964025)

Origin: backport, https://github.com/net-ssh/net-ssh/pull/864

7363613... by Antonio Terceiro on 2022-02-21

1:6.1.0-3 (patches unapplied)

Imported using git-ubuntu import.

diff --git a/debian/changelog b/debian/changelog
index 9d13b4e..ef64464 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,3 +1,11 @@
+ruby-net-ssh (1:6.1.0-3ubuntu0.1) jammy; urgency=medium
+
+  * d/p/openssl-3/*.patch: backport upstream patches to support OpenSSL 3
+    (LP: #1964025).
+  * d/ruby-tests.rake: use custom OpenSSL config file if using OpenSSL 3.
+
+ -- Lucas Kanashiro <[e-mail]>  Mon, 09 May 2022 18:44:20 -0300
+
 ruby-net-ssh (1:6.1.0-3) unstable; urgency=medium
 
   * Team upload
diff --git a/debian/control b/debian/control
index 62920fb..2483e6d 100644
--- a/debian/control
+++ b/debian/control
@@ -1,7 +1,8 @@
 Source: ruby-net-ssh
 Section: ruby
 Priority: optional
-Maintainer: Debian Ruby Team <[e-mail]>
+Maintainer: Ubuntu Developers <[e-mail]>
+XSBC-Original-Maintainer: Debian Ruby Team <[e-mail]>
 Uploaders: Lucas Nussbaum <[e-mail]>,
            Paul van Tilburg <[e-mail]>,
            David Suárez <[e-mail]>
diff --git a/debian/patches/openssl-3/0002-Generate-all-DSA-keys-with-1024-bits.patch b/debian/patches/openssl-3/0002-Generate-all-DSA-keys-with-1024-bits.patch
new file mode 100644
index 0000000..0c63bee
--- /dev/null
+++ b/debian/patches/openssl-3/0002-Generate-all-DSA-keys-with-1024-bits.patch
@@ -0,0 +1,134 @@
+From: Simon Chopin <[e-mail]>
+Date: Fri, 8 Apr 2022 09:49:06 +0200
+Subject: Generate all DSA keys with 1024 bits
+
+512bits keys are refused in newer OpenSSL libraries as too weak.
+
+Co-authored-by: Lucas Kanashiro <[e-mail]>
+---
+ test/authentication/methods/test_hostbased.rb |  2 +-
+ test/authentication/methods/test_publickey.rb |  2 +-
+ test/authentication/test_agent.rb             | 12 ++++++------
+ test/authentication/test_key_manager.rb       |  4 ++--
+ test/integration/test_agent.rb                |  2 +-
+ 5 files changed, 11 insertions(+), 11 deletions(-)
+
+Origin: backport, https://github.com/net-ssh/net-ssh/commit/6364a20037fe8
+Bug-Upstream: https://github.com/net-ssh/net-ssh/issues/843
+Bug-Ubuntu: https://bugs.launchpad.net/ubuntu/+source/ruby-net-ssh/+bug/1964025
+Reviewed-By: Lucas Kanashiro <[e-mail]>
+Last-Updated: 2022-05-09
+
+diff --git a/test/authentication/methods/test_hostbased.rb b/test/authentication/methods/test_hostbased.rb
+index 4fbd37a..957a83e 100644
+--- a/test/authentication/methods/test_hostbased.rb
++++ b/test/authentication/methods/test_hostbased.rb
+@@ -76,7 +76,7 @@ module Authentication
+ 
+       @@keys = nil
+       def keys
+-        @@keys ||= [OpenSSL::PKey::RSA.new(512), OpenSSL::PKey::DSA.new(512)]
++        @@keys ||= [OpenSSL::PKey::RSA.new(512), OpenSSL::PKey::DSA.new(1024)]
+       end
+ 
+       def key_manager(options={})
+diff --git a/test/authentication/methods/test_publickey.rb b/test/authentication/methods/test_publickey.rb
+index 8f2cc73..449f74d 100644
+--- a/test/authentication/methods/test_publickey.rb
++++ b/test/authentication/methods/test_publickey.rb
+@@ -128,7 +128,7 @@ module Authentication
+ 
+       @@keys = nil
+       def keys
+-        @@keys ||= [OpenSSL::PKey::RSA.new(512), OpenSSL::PKey::DSA.new(512)]
++        @@keys ||= [OpenSSL::PKey::RSA.new(512), OpenSSL::PKey::DSA.new(1024)]
+       end
+ 
+       def key_manager(options={})
+diff --git a/test/authentication/test_agent.rb b/test/authentication/test_agent.rb
+index 81ca477..42cc215 100644
+--- a/test/authentication/test_agent.rb
++++ b/test/authentication/test_agent.rb
+@@ -119,7 +119,7 @@ module Authentication
+ 
+     def test_identities_should_augment_identities_with_comment_field
+       key1 = key
+-      key2 = OpenSSL::PKey::DSA.new(512)
++      key2 = OpenSSL::PKey::DSA.new(1024)
+ 
+       socket.expect do |s, type, buffer|
+         assert_equal SSH2_AGENT_REQUEST_IDENTITIES, type
+@@ -135,9 +135,9 @@ module Authentication
+ 
+     def test_identities_should_ignore_unimplemented_ones
+       key1 = key
+-      key2 = OpenSSL::PKey::DSA.new(512)
++      key2 = OpenSSL::PKey::DSA.new(1024)
+       key2.to_blob[0..5] = 'badkey'
+-      key3 = OpenSSL::PKey::DSA.new(512)
++      key3 = OpenSSL::PKey::DSA.new(1024)
+ 
+       socket.expect do |s, type, buffer|
+         assert_equal SSH2_AGENT_REQUEST_IDENTITIES, type
+@@ -155,7 +155,7 @@ module Authentication
+     def test_identities_should_ignore_invalid_ones
+       key1 = key
+       key2_bad = Net::SSH::Buffer.new("")
+-      key3 = OpenSSL::PKey::DSA.new(512)
++      key3 = OpenSSL::PKey::DSA.new(1024)
+ 
+       socket.expect do |s, type, buffer|
+         assert_equal SSH2_AGENT_REQUEST_IDENTITIES, type
+@@ -251,7 +251,7 @@ module Authentication
+     end
+ 
+     def test_add_dsa_identity
+-      dsa = OpenSSL::PKey::DSA.new(512)
++      dsa = OpenSSL::PKey::DSA.new(1024)
+       socket.expect do |s,type,buffer|
+         assert_equal SSH2_AGENT_ADD_IDENTITY, type
+         assert_equal buffer.read_string, "ssh-dss"
+@@ -270,7 +270,7 @@ module Authentication
+     end
+ 
+     def test_add_dsa_cert_identity
+-      cert = make_cert(OpenSSL::PKey::DSA.new(512))
++      cert = make_cert(OpenSSL::PKey::DSA.new(1024))
+       socket.expect do |s,type,buffer|
+         assert_equal SSH2_AGENT_ADD_IDENTITY, type
+         assert_equal buffer.read_string, "[e-mail]"
+diff --git a/test/authentication/test_key_manager.rb b/test/authentication/test_key_manager.rb
+index c40779f..5f38d73 100644
+--- a/test/authentication/test_key_manager.rb
++++ b/test/authentication/test_key_manager.rb
+@@ -317,7 +317,7 @@ module Authentication
+         cert.critical_options = {}
+         cert.extensions = {}
+         cert.reserved = ''
+-        cert.sign!(OpenSSL::PKey::DSA.new(512))
++        cert.sign!(OpenSSL::PKey::DSA.new(1024))
+         cert
+       end
+     end
+@@ -327,7 +327,7 @@ module Authentication
+     end
+ 
+     def dsa
+-      @dsa ||= OpenSSL::PKey::DSA.new(512)
++      @dsa ||= OpenSSL::PKey::DSA.new(1024)
+     end
+ 
+     def ecdsa_sha2_nistp256
+diff --git a/test/integration/test_agent.rb b/test/integration/test_agent.rb
+index 4045c9a..e7db62c 100644
+--- a/test/integration/test_agent.rb
++++ b/test/integration/test_agent.rb
+@@ -19,7 +19,7 @@ class TestAgent < NetSSHTest
+   def setup
+     @keys = [
+       OpenSSL::PKey::RSA.new(1024),
+-      OpenSSL::PKey::DSA.new(512),
++      OpenSSL::PKey::DSA.new(1024),
+       OpenSSL::PKey::EC.new("prime256v1").generate_key
+     ]
+     @keys << Net::SSH::Authentication::ED25519::PrivKey.read(ED25519, nil) if Net::SSH::Authentication::ED25519Loader::LOADED
diff --git a/debian/patches/openssl-3/0003-tests-Enable-legacy-providers-if-using-OpenSSL-3.0.patch b/debian/patches/openssl-3/0003-tests-Enable-legacy-providers-if-using-OpenSSL-3.0.patch
new file mode 100644
index 0000000..2a5f342
--- /dev/null
+++ b/debian/patches/openssl-3/0003-tests-Enable-legacy-providers-if-using-OpenSSL-3.0.patch
@@ -0,0 +1,68 @@
+From: Simon Chopin <[e-mail]>
+Date: Wed, 6 Apr 2022 18:43:57 +0200
+Subject: tests: Enable legacy providers if using OpenSSL 3.0
+
+Quite a few tests rely on outdated algorithms that have been relegated
+to the legacy provider in OpenSSL 3.0. `rake test` now loads a custom
+OpenSSL configuration file to enable said legacy provider, which is
+usually disabled by default.
+---
+ Rakefile           |  6 ++++++
+ test/openssl3.conf | 25 +++++++++++++++++++++++++
+ 2 files changed, 31 insertions(+)
+ create mode 100644 test/openssl3.conf
+
+Origin: upstream, https://github.com/net-ssh/net-ssh/commit/e4ffdc07b1f0f
+Bug-Upstream: https://github.com/net-ssh/net-ssh/issues/843
+Bug-Ubuntu: https://bugs.launchpad.net/ubuntu/+source/ruby-net-ssh/+bug/1964025
+Reviewed-By: Lucas Kanashiro <[e-mail]>
+Last-Updated: 2022-05-09
+
+diff --git a/Rakefile b/Rakefile
+index 0271797..3720209 100644
+--- a/Rakefile
++++ b/Rakefile
+@@ -94,6 +94,12 @@ Rake::TestTask.new do |t|
+   t.test_files = test_files
+ end
+ 
++# We need to enable the OpenSSL 3.0 legacy providers for our test suite
++require 'openssl'
++if OpenSSL::OPENSSL_LIBRARY_VERSION.start_with? "OpenSSL 3" then
++  ENV['OPENSSL_CONF'] = 'test/openssl3.conf'
++end
++
+ desc "Run tests of Net::SSH:Test"
+ Rake::TestTask.new do |t|
+   t.name = "test_test"
+diff --git a/test/openssl3.conf b/test/openssl3.conf
+new file mode 100644
+index 0000000..79bae9a
+--- /dev/null
++++ b/test/openssl3.conf
+@@ -0,0 +1,25 @@
++openssl_conf = openssl_init
++
++[openssl_init]
++ssl_conf = ssl_sect
++providers = provider_sect
++
++[provider_sect]
++default = default_sect
++legacy = legacy_sect
++
++[default_sect]
++activate = 1
++
++[legacy_sect]
++activate = 1
++
++[ssl_sect]
++system_default = system_default_sect
++
++[system_default_sect]
++CipherString = DEFAULT@SECLEVEL=0
++# system_default = system_default_sect
++# 
++# [system_default_sect]
++# Options = UnsafeLegacyRenegotiation
diff --git a/debian/patches/openssl-3/0004-buffer-create-RSA-keys-by-loading-PEM-data-directly.patch b/debian/patches/openssl-3/0004-buffer-create-RSA-keys-by-loading-PEM-data-directly.patch
new file mode 100644
index 0000000..328ee32
--- /dev/null
+++ b/debian/patches/openssl-3/0004-buffer-create-RSA-keys-by-loading-PEM-data-directly.patch
@@ -0,0 +1,103 @@
+From: Simon Chopin <[e-mail]>
+Date: Fri, 8 Apr 2022 09:32:24 +0200
+Subject: buffer: create RSA keys by loading PEM data directly
+
+The OpenSSL 3.0 changes don't allow for us to modify the private key
+details directly, and there are no dedicated constructors as of Ruby
+3.0, so we need to actually create a PEM certificate in-memory and load
+that instead.
+
+Co-authored-by: Lucas Kanashiro <[e-mail]>
+---
+ lib/net/ssh/buffer.rb    | 18 +++++++++---------
+ test/test_buffer.rb      | 16 +++++++++-------
+ test/test_known_hosts.rb | 15 +++++++--------
+ 3 files changed, 25 insertions(+), 24 deletions(-)
+
+Origin: upstream, https://github.com/net-ssh/net-ssh/commit/406063de2852cab
+Bug-Upstream: https://github.com/net-ssh/net-ssh/issues/843
+Bug-Ubuntu: https://bugs.launchpad.net/ubuntu/+source/ruby-net-ssh/+bug/1964025
+Reviewed-By: Lucas Kanashiro <[e-mail]>
+Last-Updated: 2022-05-09
+
+diff --git a/lib/net/ssh/buffer.rb b/lib/net/ssh/buffer.rb
+index 0fe4e56..0384299 100644
+--- a/lib/net/ssh/buffer.rb
++++ b/lib/net/ssh/buffer.rb
+@@ -309,15 +309,15 @@ module Net
+             key.pub_key = read_bignum
+           end
+         when /^ssh-rsa$/
+-          key = OpenSSL::PKey::RSA.new
+-          if key.respond_to?(:set_key)
+-            e = read_bignum
+-            n = read_bignum
+-            key.set_key(n, e, nil)
+-          else
+-            key.e = read_bignum
+-            key.n = read_bignum
+-          end
++          e = read_bignum
++          n = read_bignum
++
++          asn1 = OpenSSL::ASN1::Sequence([
++            OpenSSL::ASN1::Integer(n),
++            OpenSSL::ASN1::Integer(e)
++          ])
++
++          key = OpenSSL::PKey::RSA.new(asn1.to_der)
+         when /^ssh-ed25519$/
+           Net::SSH::Authentication::ED25519Loader.raiseUnlessLoaded("unsupported key type `#{type}'")
+           key = Net::SSH::Authentication::ED25519::PubKey.read_keyblob(self)
+diff --git a/test/test_buffer.rb b/test/test_buffer.rb
+index e1fcbd2..b74e2f1 100644
+--- a/test/test_buffer.rb
++++ b/test/test_buffer.rb
+@@ -336,13 +336,15 @@ class TestBuffer < NetSSHTest
+   def test_write_rsa_key_should_write_argument_to_end_of_buffer
+     buffer = new("start")
+ 
+-    key = OpenSSL::PKey::RSA.new
+-    if key.respond_to?(:set_key)
+-      key.set_key(0x7766554433221100, 0xffeeddccbbaa9988, nil)
+-    else
+-      key.e = 0xffeeddccbbaa9988
+-      key.n = 0x7766554433221100
+-    end
++    n = 0x7766554433221100
++    e = 0xffeeddccbbaa9988
++
++    asn1 = OpenSSL::ASN1::Sequence([
++      OpenSSL::ASN1::Integer(n),
++      OpenSSL::ASN1::Integer(e)
++    ])
++
++    key = OpenSSL::PKey::RSA.new(asn1.to_der)
+ 
+     buffer.write_key(key)
+     assert_equal "start\0\0\0\7ssh-rsa\0\0\0\011\0\xff\xee\xdd\xcc\xbb\xaa\x99\x88\0\0\0\010\x77\x66\x55\x44\x33\x22\x11\x00", buffer.to_s
+diff --git a/test/test_known_hosts.rb b/test/test_known_hosts.rb
+index 6b1fda6..187f6ac 100644
+--- a/test/test_known_hosts.rb
++++ b/test/test_known_hosts.rb
+@@ -132,13 +132,12 @@ class TestKnownHosts < NetSSHTest
+   end
+ 
+   def rsa_key
+-    key = OpenSSL::PKey::RSA.new
+-    if key.respond_to?(:set_key)
+-      key.set_key(0x7766554433221100, 0xffeeddccbbaa9988, nil)
+-    else
+-      key.e = 0xffeeddccbbaa9988
+-      key.n = 0x7766554433221100
+-    end
+-    key
++    n = 0x7766554433221100
++    e = 0xffeeddccbbaa9988
++    asn1 = OpenSSL::ASN1::Sequence([
++      OpenSSL::ASN1::Integer(n),
++      OpenSSL::ASN1::Integer(e)
++    ])
++    OpenSSL::PKey::RSA.new(asn1.to_der)
+   end
+ end
diff --git a/debian/patches/openssl-3/0005-buffer-create-DSA-keys-by-loading-PEM-data-directly.patch b/debian/patches/openssl-3/0005-buffer-create-DSA-keys-by-loading-PEM-data-directly.patch
new file mode 100644
index 0000000..c29b87c
--- /dev/null
+++ b/debian/patches/openssl-3/0005-buffer-create-DSA-keys-by-loading-PEM-data-directly.patch
@@ -0,0 +1,106 @@
+From: Simon Chopin <[e-mail]>
+Date: Fri, 8 Apr 2022 09:32:24 +0200
+Subject: buffer: create DSA keys by loading PEM data directly
+
+The OpenSSL 3.0 changes don't allow for us to modify the private key
+details directly, and there are no dedicated constructors as of Ruby
+3.0, so we need to actually create a PEM certificate in-memory and load
+that instead.
+
+To add insult to injury, contrary to other types of keys such as RSA, we
+need to actually build the full PEM data and not just pack the numbers
+in a simple sequence, making the code even a bit more complicated.
+
+Co-authored-by: Lucas Kanashiro <[e-mail]>
+---
+ lib/net/ssh/buffer.rb | 31 ++++++++++++++++++-------------
+ test/test_buffer.rb   | 28 ++++++++++++++++++----------
+ 2 files changed, 36 insertions(+), 23 deletions(-)
+
+Origin: upstream, https://github.com/net-ssh/net-ssh/commit/406063de2852
+Bug-Upstream: https://github.com/net-ssh/net-ssh/issues/843
+Bug-Ubuntu: https://bugs.launchpad.net/ubuntu/+source/ruby-net-ssh/+bug/1964025
+Reviewed-By: Lucas Kanashiro <[e-mail]>
+Last-Updated: 2022-05-09
+
+diff --git a/lib/net/ssh/buffer.rb b/lib/net/ssh/buffer.rb
+index 0384299..5a7dff0 100644
+--- a/lib/net/ssh/buffer.rb
++++ b/lib/net/ssh/buffer.rb
+@@ -295,19 +295,24 @@ module Net
+         when /^(.*)-cert-v01@openssh\.com$/
+           key = Net::SSH::Authentication::Certificate.read_certblob(self, $1)
+         when /^ssh-dss$/
+-          key = OpenSSL::PKey::DSA.new
+-          if key.respond_to?(:set_pqg)
+-            key.set_pqg(read_bignum, read_bignum, read_bignum)
+-          else
+-            key.p = read_bignum
+-            key.q = read_bignum
+-            key.g = read_bignum
+-          end
+-          if key.respond_to?(:set_key)
+-            key.set_key(read_bignum, nil)
+-          else
+-            key.pub_key = read_bignum
+-          end
++          p = read_bignum
++          q = read_bignum
++          g = read_bignum
++          pub_key = read_bignum
++
++          asn1 = OpenSSL::ASN1::Sequence.new([
++            OpenSSL::ASN1::Sequence.new([
++              OpenSSL::ASN1::ObjectId.new('DSA'),
++              OpenSSL::ASN1::Sequence.new([
++                OpenSSL::ASN1::Integer.new(p),
++                OpenSSL::ASN1::Integer.new(q),
++                OpenSSL::ASN1::Integer.new(g)
++              ]),
++            ]),
++            OpenSSL::ASN1::BitString.new(OpenSSL::ASN1::Integer.new(pub_key).to_der)
++          ])
++
++          key = OpenSSL::PKey::DSA.new(asn1.to_der)
+         when /^ssh-rsa$/
+           e = read_bignum
+           n = read_bignum
+diff --git a/test/test_buffer.rb b/test/test_buffer.rb
+index b74e2f1..f75a729 100644
+--- a/test/test_buffer.rb
++++ b/test/test_buffer.rb
+@@ -318,16 +318,24 @@ class TestBuffer < NetSSHTest
+   def test_write_dss_key_should_write_argument_to_end_of_buffer
+     buffer = new("start")
+ 
+-    key = OpenSSL::PKey::DSA.new
+-    if key.respond_to?(:set_pqg)
+-      key.set_pqg(0xffeeddccbbaa9988, 0x7766554433221100, 0xffddbb9977553311)
+-      key.set_key(0xeeccaa8866442200, nil)
+-    else
+-      key.p = 0xffeeddccbbaa9988
+-      key.q = 0x7766554433221100
+-      key.g = 0xffddbb9977553311
+-      key.pub_key = 0xeeccaa8866442200
+-    end
++    p = 0xffeeddccbbaa9988
++    q = 0x7766554433221100
++    g = 0xffddbb9977553311
++    pub_key = 0xeeccaa8866442200
++
++    asn1 = OpenSSL::ASN1::Sequence.new([
++      OpenSSL::ASN1::Sequence.new([
++        OpenSSL::ASN1::ObjectId.new('DSA'),
++        OpenSSL::ASN1::Sequence.new([
++          OpenSSL::ASN1::Integer.new(p),
++          OpenSSL::ASN1::Integer.new(q),
++          OpenSSL::ASN1::Integer.new(g)
++        ]),
++      ]),
++      OpenSSL::ASN1::BitString.new(OpenSSL::ASN1::Integer.new(pub_key).to_der)
++    ])
++
++    key = OpenSSL::PKey::DSA.new(asn1.to_der)
+ 
+     buffer.write_key(key)
+     assert_equal "start\0\0\0\7ssh-dss\0\0\0\011\0\xff\xee\xdd\xcc\xbb\xaa\x99\x88\0\0\0\010\x77\x66\x55\x44\x33\x22\x11\x00\0\0\0\011\0\xff\xdd\xbb\x99\x77\x55\x33\x11\0\0\0\011\0\xee\xcc\xaa\x88\x66\x44\x22\x00", buffer.to_s
diff --git a/debian/patches/openssl-3/0006-transport-create-EC-keys-by-loading-PEM-data-directl.patch b/debian/patches/openssl-3/0006-transport-create-EC-keys-by-loading-PEM-data-directl.patch
new file mode 100644
index 0000000..438cdba
--- /dev/null
+++ b/debian/patches/openssl-3/0006-transport-create-EC-keys-by-loading-PEM-data-directl.patch
@@ -0,0 +1,46 @@
+From: Simon Chopin <[e-mail]>
+Date: Fri, 8 Apr 2022 09:32:24 +0200
+Subject: transport: create EC keys by loading PEM data directly
+
+The OpenSSL 3.0 changes don't allow for us to modify the private key
+details directly, and there are no dedicated constructors as of Ruby
+3.0, so we need to actually create a PEM certificate in-memory and load
+that instead.
+
+Co-authored-by: Lucas Kanashiro <[e-mail]>
+---
+ lib/net/ssh/transport/openssl.rb | 14 +++++++++++---
+ 1 file changed, 11 insertions(+), 3 deletions(-)
+
+Origin: upstream, https://github.com/net-ssh/net-ssh/commit/4de6831dea
+Bug-Upstream: https://github.com/net-ssh/net-ssh/issues/843
+Bug-Ubuntu: https://bugs.launchpad.net/ubuntu/+source/ruby-net-ssh/+bug/1964025
+Reviewed-By: Lucas Kanashiro <[e-mail]>
+Last-Updated: 2022-05-09
+
+diff --git a/lib/net/ssh/transport/openssl.rb b/lib/net/ssh/transport/openssl.rb
+index 0581dd5..c5ff2fb 100644
+--- a/lib/net/ssh/transport/openssl.rb
++++ b/lib/net/ssh/transport/openssl.rb
+@@ -147,10 +147,18 @@ module OpenSSL
+ 
+         public_key_oct = buffer.read_string
+         begin
+-          key = OpenSSL::PKey::EC.new(OpenSSL::PKey::EC::CurveNameAlias[curve_name_in_key])
+-          group = key.group
++          curvename = OpenSSL::PKey::EC::CurveNameAlias[curve_name_in_key]
++          group = OpenSSL::PKey::EC::Group.new(curvename)
+           point = OpenSSL::PKey::EC::Point.new(group, OpenSSL::BN.new(public_key_oct, 2))
+-          key.public_key = point
++          asn1 = OpenSSL::ASN1::Sequence([
++            OpenSSL::ASN1::Sequence([
++              OpenSSL::ASN1::ObjectId("id-ecPublicKey"),
++              OpenSSL::ASN1::ObjectId(curvename)
++            ]),
++            OpenSSL::ASN1::BitString(point.to_octet_string(:uncompressed))
++          ])
++
++          key = OpenSSL::PKey::EC.new(asn1.to_der)
+ 
+           return key
+         rescue OpenSSL::PKey::ECError
diff --git a/debian/patches/openssl-3/0007-Use-OpenSSL-PKey-EC.generate-static-method.patch b/debian/patches/openssl-3/0007-Use-OpenSSL-PKey-EC.generate-static-method.patch
new file mode 100644
index 0000000..93a87c0
--- /dev/null
+++ b/debian/patches/openssl-3/0007-Use-OpenSSL-PKey-EC.generate-static-method.patch
@@ -0,0 +1,147 @@
+From: Simon Chopin <[e-mail]>
+Date: Mon, 11 Apr 2022 16:25:39 +0200
+Subject: Use OpenSSL::PKey::EC.generate static method
+
+Migrate all instances of the pattern EC.new(foo).generate_key to
+EC.generate(foo), as the old pattern isn't supported when using OpenSSL
+3.0, since one is not allowed to mess with the internal data of already
+created objects now.
+
+The new API has been introduced in Ruby 2.4.
+
+Co-authored-by: Lucas Kanashiro <[e-mail]>
+---
+ lib/net/ssh/transport/kex/ecdh_sha2_nistp256.rb | 2 +-
+ test/authentication/test_agent.rb               | 4 ++--
+ test/authentication/test_key_manager.rb         | 6 +++---
+ test/test_buffer.rb                             | 6 +++---
+ test/transport/kex/test_curve25519_sha256.rb    | 2 +-
+ test/transport/kex/test_ecdh_sha2_nistp256.rb   | 4 ++--
+ 6 files changed, 12 insertions(+), 12 deletions(-)
+
+Origin: backport, https://github.com/net-ssh/net-ssh/commit/8729d47045b
+Bug-Upstream: https://github.com/net-ssh/net-ssh/issues/843
+Bug-Ubuntu: https://bugs.launchpad.net/ubuntu/+source/ruby-net-ssh/+bug/1964025
+Reviewed-By: Lucas Kanashiro <[e-mail]>
+Last-Updated: 2022-05-09
+
+diff --git a/lib/net/ssh/transport/kex/ecdh_sha2_nistp256.rb b/lib/net/ssh/transport/kex/ecdh_sha2_nistp256.rb
+index 84d0e4a..a0b2d73 100644
+--- a/lib/net/ssh/transport/kex/ecdh_sha2_nistp256.rb
++++ b/lib/net/ssh/transport/kex/ecdh_sha2_nistp256.rb
+@@ -18,7 +18,7 @@ module Net
+           private
+ 
+           def generate_key #:nodoc:
+-            OpenSSL::PKey::EC.new(curve_name).generate_key
++            OpenSSL::PKey::EC.generate(curve_name)
+           end
+ 
+           # compute shared secret from server's public key and client's private key
+diff --git a/test/authentication/test_agent.rb b/test/authentication/test_agent.rb
+index 42cc215..253317f 100644
+--- a/test/authentication/test_agent.rb
++++ b/test/authentication/test_agent.rb
+@@ -286,7 +286,7 @@ module Authentication
+     end
+ 
+     def test_add_ecdsa_identity
+-      ecdsa = OpenSSL::PKey::EC.new("prime256v1").generate_key
++      ecdsa = OpenSSL::PKey::EC.generate("prime256v1")
+       socket.expect do |s,type,buffer|
+         assert_equal SSH2_AGENT_ADD_IDENTITY, type
+         assert_equal buffer.read_string, "ecdsa-sha2-nistp256"
+@@ -303,7 +303,7 @@ module Authentication
+     end
+ 
+     def test_add_ecdsa_cert_identity
+-      cert = make_cert(OpenSSL::PKey::EC.new("prime256v1").generate_key)
++      cert = make_cert(OpenSSL::PKey::EC.generate("prime256v1"))
+       socket.expect do |s,type,buffer|
+         assert_equal SSH2_AGENT_ADD_IDENTITY, type
+         assert_equal buffer.read_string, "[e-mail]"
+diff --git a/test/authentication/test_key_manager.rb b/test/authentication/test_key_manager.rb
+index 5f38d73..06a4594 100644
+--- a/test/authentication/test_key_manager.rb
++++ b/test/authentication/test_key_manager.rb
+@@ -331,15 +331,15 @@ module Authentication
+     end
+ 
+     def ecdsa_sha2_nistp256
+-      @ecdsa_sha2_nistp256 ||= OpenSSL::PKey::EC.new('prime256v1').generate_key
++      @ecdsa_sha2_nistp256 ||= OpenSSL::PKey::EC.generate('prime256v1')
+     end
+ 
+     def ecdsa_sha2_nistp384
+-      @ecdsa_sha2_nistp384 ||= OpenSSL::PKey::EC.new('secp384r1').generate_key
++      @ecdsa_sha2_nistp384 ||= OpenSSL::PKey::EC.generate('secp384r1')
+     end
+ 
+     def ecdsa_sha2_nistp521
+-      @ecdsa_sha2_nistp521 ||= OpenSSL::PKey::EC.new('secp521r1').generate_key
++      @ecdsa_sha2_nistp521 ||= OpenSSL::PKey::EC.generate('secp521r1')
+     end
+ 
+     def rsa_pk
+diff --git a/test/test_buffer.rb b/test/test_buffer.rb
+index f75a729..57b98e5 100644
+--- a/test/test_buffer.rb
++++ b/test/test_buffer.rb
+@@ -456,7 +456,7 @@ class TestBuffer < NetSSHTest
+   end
+ 
+   def random_ecdsa_sha2_nistp256
+-    k = OpenSSL::PKey::EC.new('prime256v1').generate_key
++    k = OpenSSL::PKey::EC.generate('prime256v1')
+     buffer = Net::SSH::Buffer.from(:string, 'nistp256',
+                                    :string, k.public_key.to_bn.to_s(2))
+     key = yield(buffer)
+@@ -465,7 +465,7 @@ class TestBuffer < NetSSHTest
+   end
+ 
+   def random_ecdsa_sha2_nistp384
+-    k = OpenSSL::PKey::EC.new('secp384r1').generate_key
++    k = OpenSSL::PKey::EC.generate('secp384r1')
+     buffer = Net::SSH::Buffer.from(:string, 'nistp384',
+                                    :string, k.public_key.to_bn.to_s(2))
+     key = yield(buffer)
+@@ -474,7 +474,7 @@ class TestBuffer < NetSSHTest
+   end
+ 
+   def random_ecdsa_sha2_nistp521
+-    k = OpenSSL::PKey::EC.new('secp521r1').generate_key
++    k = OpenSSL::PKey::EC.generate('secp521r1')
+     buffer = Net::SSH::Buffer.from(:string, 'nistp521',
+                                    :string, k.public_key.to_bn.to_s(2))
+     key = yield(buffer)
+diff --git a/test/transport/kex/test_curve25519_sha256.rb b/test/transport/kex/test_curve25519_sha256.rb
+index 8177a38..d990019 100644
+--- a/test/transport/kex/test_curve25519_sha256.rb
++++ b/test/transport/kex/test_curve25519_sha256.rb
+@@ -111,7 +111,7 @@ unless ENV['NET_SSH_NO_ED25519']
+         end
+ 
+         def server_host_key
+-          @server_host_key ||= OpenSSL::PKey::EC.new('prime256v1').generate_key
++          @server_host_key ||= OpenSSL::PKey::EC.generate('prime256v1')
+         end
+ 
+         def packet_data
+diff --git a/test/transport/kex/test_ecdh_sha2_nistp256.rb b/test/transport/kex/test_ecdh_sha2_nistp256.rb
+index 932d8d7..a2ed6b4 100644
+--- a/test/transport/kex/test_ecdh_sha2_nistp256.rb
++++ b/test/transport/kex/test_ecdh_sha2_nistp256.rb
+@@ -109,11 +109,11 @@ module Transport
+       end
+ 
+       def server_key
+-        @server_key ||= OpenSSL::PKey::EC.new(ecparam).generate_key
++        @server_key ||= OpenSSL::PKey::EC.generate(ecparam)
+       end
+ 
+       def server_host_key
+-        @server_host_key ||= OpenSSL::PKey::EC.new('prime256v1').generate_key
++        @server_host_key ||= OpenSSL::PKey::EC.generate('prime256v1')
+       end
+ 
+       def packet_data
diff --git a/debian/patches/openssl-3/0008-diffie-hellman-create-the-key-by-generating-the-PEM-.patch b/debian/patches/openssl-3/0008-diffie-hellman-create-the-key-by-generating-the-PEM-.patch
new file mode 100644
index 0000000..623e2e6
--- /dev/null
+++ b/debian/patches/openssl-3/0008-diffie-hellman-create-the-key-by-generating-the-PEM-.patch
@@ -0,0 +1,70 @@
+From: Simon Chopin <[e-mail]>
+Date: Mon, 11 Apr 2022 16:04:08 +0200
+Subject: diffie-hellman: create the key by generating the PEM file
+
+This makes the code compatible with OpenSSL 3.0. However, an issue with
+this is that it is not possible anymore to ensure a specific size for
+the private key, as indicated in the inline comment.
+
+v2: avoid PKey.generate_key on older releases (< 2.7)
+
+Co-authored-by: Lucas Kanashiro <[e-mail]>
+---
+ .../transport/kex/diffie_hellman_group1_sha1.rb    | 36 +++++++++++-----------
+ 1 file changed, 18 insertions(+), 18 deletions(-)
+
+Origin: backport, https://github.com/net-ssh/net-ssh/commit/8929562bec
+Bug-Upstream: https://github.com/net-ssh/net-ssh/issues/843
+Bug-Ubuntu: https://bugs.launchpad.net/ubuntu/+source/ruby-net-ssh/+bug/1964025
+Reviewed-By: Lucas Kanashiro <[e-mail]>
+Last-Updated: 2022-05-09
+
+diff --git a/lib/net/ssh/transport/kex/diffie_hellman_group1_sha1.rb b/lib/net/ssh/transport/kex/diffie_hellman_group1_sha1.rb
+index 34af18b..a78b5d5 100644
+--- a/lib/net/ssh/transport/kex/diffie_hellman_group1_sha1.rb
++++ b/lib/net/ssh/transport/kex/diffie_hellman_group1_sha1.rb
+@@ -59,26 +59,26 @@ module Net
+ 
+           # Generate a DH key with a private key consisting of the given
+           # number of bytes.
+-          def generate_key #:nodoc:
+-            dh = OpenSSL::PKey::DH.new
+-
+-            if dh.respond_to?(:set_pqg)
+-              p, g = get_parameters
+-              dh.set_pqg(p, nil, g)
++          def generate_key # :nodoc:
++            p, g = get_parameters
++
++            asn1 = OpenSSL::ASN1::Sequence(
++              [
++                OpenSSL::ASN1::Integer(p),
++                OpenSSL::ASN1::Integer(g)
++              ]
++            )
++
++            dh_params = OpenSSL::PKey::DH.new(asn1.to_der)
++            # XXX No private key size check! In theory the latter call should work but fails on OpenSSL 3.0 as
++            # dh_paramgen_subprime_len is now reserved for DHX algorithm
++            # key = OpenSSL::PKey.generate_key(dh_params, "dh_paramgen_subprime_len" => data[:need_bytes]/8)
++            if OpenSSL::PKey.respond_to?(:generate_key)
++              OpenSSL::PKey.generate_key(dh_params)
+             else
+-              dh.p, dh.g = get_parameters
+-            end
+-
+-            dh.generate_key!
+-            until dh.valid? && dh.priv_key.num_bytes == data[:need_bytes]
+-              if dh.respond_to?(:set_key)
+-                dh.set_key(nil, OpenSSL::BN.rand(data[:need_bytes] * 8))
+-              else
+-                dh.priv_key = OpenSSL::BN.rand(data[:need_bytes] * 8)
+-              end
+-              dh.generate_key!
++              dh_params.generate_key!
++              dh_params
+             end
+-            dh
+           end
+ 
+           # Send the KEXDH_INIT message, and expect the KEXDH_REPLY. Return the
diff --git a/debian/patches/openssl-3/0009-Fix-unit-tests-for-OpenSSL-3.patch b/debian/patches/openssl-3/0009-Fix-unit-tests-for-OpenSSL-3.patch
new file mode 100644
index 0000000..4e393ca
--- /dev/null
+++ b/debian/patches/openssl-3/0009-Fix-unit-tests-for-OpenSSL-3.patch
@@ -0,0 +1,65 @@
+From: Florian Wininger <[e-mail]>
+Date: Fri, 29 Apr 2022 14:19:55 +0200
+Subject: Fix unit tests for OpenSSL 3
+
+---
+ test/common.rb                                        | 12 ++++++++++++
+ test/transport/kex/test_diffie_hellman_group1_sha1.rb |  2 +-
+ test/transport/test_algorithms.rb                     |  2 +-
+ 3 files changed, 14 insertions(+), 2 deletions(-)
+
+Origin: upstream, https://github.com/net-ssh/net-ssh/commit/395f0cd4029c
+Bug-Upstream: https://github.com/net-ssh/net-ssh/issues/843
+Bug-Ubuntu: https://bugs.launchpad.net/ubuntu/+source/ruby-net-ssh/+bug/1964025
+Reviewed-By: Lucas Kanashiro <[e-mail]>
+Last-Updated: 2022-05-09
+
+diff --git a/test/common.rb b/test/common.rb
+index 8ae521c..db97d60 100644
+--- a/test/common.rb
++++ b/test/common.rb
+@@ -46,6 +46,18 @@ def P(*args)
+   Net::SSH::Packet.new(Net::SSH::Buffer.from(*args))
+ end
+ 
++# DH key generate with OpenSSL::PKey::DH.new(512).to_pem
++def dh_512bits_bn
++  OpenSSL::PKey::DH.new(
++    <<~DH_KEY
++      -----BEGIN DH PARAMETERS-----
++      MEYCQQDkZMgCTieW40x/bmCpf6m1XHERNnyOodot21UsJkCidr+T6aAcy/Oz4mWo
++      aYudmZZLQz7jhz0Ut2VQUw0Nz033AgEC
++      -----END DH PARAMETERS-----
++    DH_KEY
++  ).p
++end
++
+ class NetSSHTest < Minitest::Test
+   def assert_nothing_raised(&block)
+     yield
+diff --git a/test/transport/kex/test_diffie_hellman_group1_sha1.rb b/test/transport/kex/test_diffie_hellman_group1_sha1.rb
+index be51720..d621de6 100644
+--- a/test/transport/kex/test_diffie_hellman_group1_sha1.rb
++++ b/test/transport/kex/test_diffie_hellman_group1_sha1.rb
+@@ -134,7 +134,7 @@ module Transport
+       end
+ 
+       def server_dh_pubkey
+-        @server_dh_pubkey ||= bn(1234567890)
++        @server_dh_pubkey ||= OpenSSL::BN.new(dh_512bits_bn, 10)
+       end
+ 
+       def shared_secret
+diff --git a/test/transport/test_algorithms.rb b/test/transport/test_algorithms.rb
+index 105f3af..7eb50aa 100644
+--- a/test/transport/test_algorithms.rb
++++ b/test/transport/test_algorithms.rb
+@@ -368,7 +368,7 @@ module Transport
+     end
+ 
+     def shared_secret
+-      @shared_secret ||= OpenSSL::BN.new("1234567890", 10)
++      @shared_secret ||= dh_512bits_bn
+     end
+ 
+     def session_id
diff --git a/debian/patches/series b/debian/patches/series
index cb8efb3..f7fd3ea 100644
--- a/debian/patches/series
+++ b/debian/patches/series
@@ -1 +1,9 @@
 0001-openssl-DSA-don-t-hardcode-expected-signature-size.patch
+openssl-3/0002-Generate-all-DSA-keys-with-1024-bits.patch
+openssl-3/0003-tests-Enable-legacy-providers-if-using-OpenSSL-3.0.patch
+openssl-3/0004-buffer-create-RSA-keys-by-loading-PEM-data-directly.patch
+openssl-3/0005-buffer-create-DSA-keys-by-loading-PEM-data-directly.patch
+openssl-3/0006-transport-create-EC-keys-by-loading-PEM-data-directl.patch
+openssl-3/0007-Use-OpenSSL-PKey-EC.generate-static-method.patch
+openssl-3/0008-diffie-hellman-create-the-key-by-generating-the-PEM-.patch
+openssl-3/0009-Fix-unit-tests-for-OpenSSL-3.patch
diff --git a/debian/ruby-tests.rake b/debian/ruby-tests.rake
index 751fecc..38479eb 100644
--- a/debian/ruby-tests.rake
+++ b/debian/ruby-tests.rake
@@ -3,5 +3,12 @@ require 'gem2deb/rake/testtask'
 # Unfortunately this also disables 'ed25519' tests.
 ENV['NET_SSH_NO_ED25519'] = '1'
 
+# Some tests rely no ciphers which are considered legacy in OpenSSL 3. For now,
+# let's use the custom config file to enable them and make the tests pass.
+require 'openssl'
+if OpenSSL::OPENSSL_LIBRARY_VERSION.start_with? "OpenSSL 3"
+  ENV['OPENSSL_CONF'] = Dir.pwd + '/test/openssl3.conf'
+end
+
 Gem2Deb::Rake::TestTask.new do |t|
 end