diff --git a/repos/system_upgrade/common/actors/openssl/checkopensslconf/actor.py b/repos/system_upgrade/common/actors/openssl/checkopensslconf/actor.py
new file mode 100644
index 0000000000..dd05db9c27
--- /dev/null
+++ b/repos/system_upgrade/common/actors/openssl/checkopensslconf/actor.py
@@ -0,0 +1,33 @@
+from leapp.actors import Actor
+from leapp.libraries.actor import checkopensslconf
+from leapp.models import DistributionSignedRPM, Report, TrackedFilesInfoSource
+from leapp.tags import ChecksPhaseTag, IPUWorkflowTag
+
+
+class CheckOpenSSLConf(Actor):
+    """
+    Check whether the openssl configuration and openssl-IBMCA.
+
+    See the report messages for more details. The summary is that since RHEL 8
+    it's expected to configure OpenSSL via crypto policies. Also, OpenSSL has
+    different versions between major versions of RHEL:
+      * RHEL 7: 1.0,
+      * RHEL 8: 1.1,
+      * RHEL 9: 3.0
+    So OpenSSL configuration from older system does not have to be 100%
+    compatible with the new system. In some cases, the old configuration could
+    make the system inaccessible remotely. So new approach is to ensure the
+    upgraded system will use always new default /etc/pki/tls/openssl.cnf
+    configuration file (the original one will be backed up if modified by user).
+
+    Similar for OpenSSL-IBMCA, when it's expected to configure it again on
+    each newer system.
+    """
+
+    name = 'check_openssl_conf'
+    consumes = (DistributionSignedRPM, TrackedFilesInfoSource)
+    produces = (Report,)
+    tags = (IPUWorkflowTag, ChecksPhaseTag)
+
+    def process(self):
+        checkopensslconf.process()
diff --git a/repos/system_upgrade/common/actors/openssl/checkopensslconf/libraries/checkopensslconf.py b/repos/system_upgrade/common/actors/openssl/checkopensslconf/libraries/checkopensslconf.py
new file mode 100644
index 0000000000..06a30fa102
--- /dev/null
+++ b/repos/system_upgrade/common/actors/openssl/checkopensslconf/libraries/checkopensslconf.py
@@ -0,0 +1,135 @@
+from leapp import reporting
+from leapp.libraries.common.config import architecture, version
+from leapp.libraries.common.rpms import has_package
+from leapp.libraries.stdlib import api
+from leapp.models import DistributionSignedRPM, TrackedFilesInfoSource
+
+DEFAULT_OPENSSL_CONF = '/etc/pki/tls/openssl.cnf'
+URL_8_CRYPTOPOLICIES = 'https://red.ht/rhel-8-system-wide-crypto-policies'
+URL_9_CRYPTOPOLICIES = 'https://red.ht/rhel-9-system-wide-crypto-policies'
+
+
+def check_ibmca():
+    if not architecture.matches_architecture(architecture.ARCH_S390X):
+        # not needed check really, but keeping it to make it clear
+        return
+    if not has_package(DistributionSignedRPM, 'openssl-ibmca'):
+        return
+    # In RHEL 9 has been introduced new technology: openssl providers. The engine
+    # is deprecated, so keep proper teminology to not confuse users.
+    dst_tech = 'engine' if version.get_target_major_version() == '8' else 'providers'
+    summary = (
+        'The presence of openssl-ibmca package suggests that the system may be configured'
+        ' to use the IBMCA OpenSSL engine.'
+        ' Due to major changes in OpenSSL and libica between RHEL {source} and RHEL {target} it is not'
+        ' possible to migrate OpenSSL configuration files automatically. Therefore,'
+        ' it is necessary to enable IBMCA {tech} in the OpenSSL config file manually'
+        ' after the system upgrade.'
+        .format(
+            source=version.get_source_major_version(),
+            target=version.get_target_major_version(),
+            tech=dst_tech
+        )
+    )
+
+    hint = (
+        'Configure the IBMCA {tech} manually after the upgrade.'
+        ' Please, be aware that it is not recommended to configure the system default'
+        ' {fpath}. Instead, it is recommended to configure a copy of'
+        ' that file and use this copy only for particular applications that are supposed'
+        ' to utilize the IBMCA {tech}. The location of the OpenSSL configuration file'
+        ' can be specified using the OPENSSL_CONF environment variable.'
+        .format(tech=dst_tech, fpath=DEFAULT_OPENSSL_CONF)
+    )
+
+    reporting.create_report([
+        reporting.Title('Detected possible use of IBMCA in OpenSSL'),
+        reporting.Summary(summary),
+        reporting.Remediation(hint=hint),
+        reporting.Severity(reporting.Severity.MEDIUM),
+        reporting.Groups([
+            reporting.Groups.POST,
+            reporting.Groups.ENCRYPTION
+        ]),
+    ])
+
+
+def _is_openssl_modified():
+    tracked_files = next(api.consume(TrackedFilesInfoSource), None)
+    if not tracked_files:
+        # unexpected at all, skipping testing, but keeping the log just in case
+        api.current_logger.warning('The TrackedFilesInfoSource message is missing! Skipping check of openssl config.')
+        return False
+    for finfo in tracked_files.files:
+        if finfo.path == DEFAULT_OPENSSL_CONF:
+            return finfo.is_modified
+    return False
+
+
+def check_default_openssl():
+    if not _is_openssl_modified():
+        return
+
+    crypto_url = URL_8_CRYPTOPOLICIES if version.get_target_major_version == '8' else URL_9_CRYPTOPOLICIES
+
+    # TODO(pstodulk): Needs in future some rewording, as OpenSSL engines are
+    # deprecated since "RHEL 8" and people should use OpenSSL providers instead.
+    # (IIRC, they are required to use OpenSSL providers since RHEL 9.) The
+    # current wording could be inaccurate.
+    summary = (
+        'The OpenSSL configuration file ({fpath}) has been'
+        ' modified on the system. RHEL 8 (and newer) systems provide a crypto-policies'
+        ' mechanism ensuring usage of system-wide secure cryptography algorithms.'
+        ' Also the target system uses newer version of OpenSSL that is not fully'
+        ' compatible with the current one.'
+        ' To ensure the upgraded system uses crypto-policies as expected,'
+        ' the new version of the openssl configuration file must be installed'
+        ' during the upgrade. This will be done automatically.'
+        ' The original configuration file will be saved'
+        ' as "{fpath}.leappsave".'
+        '\n\nNote this can affect the ability to connect to the system after'
+        ' the upgrade if it depends on the current OpenSSL configuration.'
+        ' Such a problem may be caused by using a particular OpenSSL engine, as'
+        ' OpenSSL engines built for the'
+        ' RHEL {source} system are not compatible with RHEL {target}.'
+        .format(
+            fpath=DEFAULT_OPENSSL_CONF,
+            source=version.get_source_major_version(),
+            target=version.get_target_major_version()
+        )
+    )
+    if version.get_target_major_version() == '9':
+        # NOTE(pstodulk): that a try to make things with engine/providers a
+        # little bit better (see my TODO note above)
+        summary += (
+            '\n\nNote the legacy ENGINE API is deprecated since RHEL 8 and'
+            ' it is required to use the new OpenSSL providers API instead on'
+            ' RHEL 9 systems.'
+        )
+    hint = (
+        'Check that your ability to login to the system does not depend on'
+        ' the OpenSSL configuration. After the upgrade, review the system configuration'
+        ' and configure the system as needed.'
+        ' Please, be aware that it is not recommended to configure the system default'
+        ' {fpath}. Instead, it is recommended to copy the file and use this copy'
+        ' to configure particular applications.'
+        ' The default OpenSSL configuration file should be modified only'
+        ' when it is really necessary.'
+    )
+    reporting.create_report([
+        reporting.Title('The /etc/pki/tls/openssl.cnf file is modified and will be replaced during the upgrade.'),
+        reporting.Summary(summary),
+        reporting.Remediation(hint=hint),
+        reporting.Severity(reporting.Severity.HIGH),
+        reporting.Groups([reporting.Groups.POST, reporting.Groups.SECURITY]),
+        reporting.RelatedResource('file', DEFAULT_OPENSSL_CONF),
+        reporting.ExternalLink(
+            title='Using system-wide cryptographic policies.',
+            url=crypto_url
+        )
+    ])
+
+
+def process():
+    check_ibmca()
+    check_default_openssl()
diff --git a/repos/system_upgrade/common/actors/openssl/checkopensslconf/tests/unit_test_checkopensslconf.py b/repos/system_upgrade/common/actors/openssl/checkopensslconf/tests/unit_test_checkopensslconf.py
new file mode 100644
index 0000000000..541ff75d48
--- /dev/null
+++ b/repos/system_upgrade/common/actors/openssl/checkopensslconf/tests/unit_test_checkopensslconf.py
@@ -0,0 +1,102 @@
+import pytest
+
+from leapp import reporting
+from leapp.libraries.actor import checkopensslconf
+from leapp.libraries.common.config import architecture
+from leapp.libraries.common.testutils import create_report_mocked, CurrentActorMocked, logger_mocked
+from leapp.libraries.stdlib import api
+from leapp.models import DistributionSignedRPM, FileInfo, RPM, TrackedFilesInfoSource
+
+_DUMP_PKG_NAMES = ['random', 'pkgs', 'openssl-ibmca-nope', 'ibmca', 'nope-openssl-ibmca']
+_SSL_CONF = checkopensslconf.DEFAULT_OPENSSL_CONF
+
+
+def _msg_pkgs(pkgnames):
+    rpms = []
+    for pname in pkgnames:
+        rpms.append(RPM(
+            name=pname,
+            epoch='0',
+            version='1.0',
+            release='1',
+            arch='noarch',
+            pgpsig='RSA/SHA256, Mon 01 Jan 1970 00:00:00 AM -03, Key ID 199e2f91fd431d51',
+            packager='Red Hat, Inc. (auxiliary key 2) <security@redhat.com>'
+
+        ))
+    return DistributionSignedRPM(items=rpms)
+
+
+@pytest.mark.parametrize('arch,pkgnames,ibmca_report', (
+    (architecture.ARCH_S390X, [], False),
+    (architecture.ARCH_S390X, _DUMP_PKG_NAMES, False),
+    (architecture.ARCH_S390X, ['openssl-ibmca'], True),
+    (architecture.ARCH_S390X, _DUMP_PKG_NAMES + ['openssl-ibmca'], True),
+    (architecture.ARCH_S390X, ['openssl-ibmca'] + _DUMP_PKG_NAMES, True),
+
+    # stay false for non-IBM-z arch - invalid scenario basically
+    (architecture.ARCH_X86_64, ['openssl-ibmca'], False),
+    (architecture.ARCH_PPC64LE, ['openssl-ibmca'], False),
+    (architecture.ARCH_ARM64, ['openssl-ibmca'], False),
+
+))
+@pytest.mark.parametrize('src_maj_ver', ('7', '8', '9'))
+def test_check_ibmca(monkeypatch, src_maj_ver, arch, pkgnames, ibmca_report):
+    monkeypatch.setattr(reporting, "create_report", create_report_mocked())
+    monkeypatch.setattr(api, 'current_actor', CurrentActorMocked(
+        arch=arch,
+        msgs=[_msg_pkgs(pkgnames)],
+        src_ver='{}.6'.format(src_maj_ver),
+        dst_ver='{}.0'.format(int(src_maj_ver) + 1)
+    ))
+    checkopensslconf.check_ibmca()
+
+    if not ibmca_report:
+        assert not reporting.create_report.called, 'IBMCA report created when it should not.'
+    else:
+        assert reporting.create_report.called, 'IBMCA report has not been created.'
+
+
+def _msg_files(fnames_changed, fnames_untouched):
+    res = []
+    for fname in fnames_changed:
+        res.append(FileInfo(
+            path=fname,
+            exists=True,
+            is_modified=True
+        ))
+
+    for fname in fnames_untouched:
+        res.append(FileInfo(
+            path=fname,
+            exists=True,
+            is_modified=False
+        ))
+
+    return TrackedFilesInfoSource(files=res)
+
+
+# NOTE(pstodulk): Ignoring situation when _SSL_CONF is missing (modified, do not exists).
+# It's not a valid scenario actually, as this file just must exists on the system to
+# consider it in a supported state.
+@pytest.mark.parametrize('msg,openssl_report', (
+    # matrix focused on openssl reports only (positive)
+    (_msg_files([], []), False),
+    (_msg_files([_SSL_CONF], []), True),
+    (_msg_files(['what/ever', _SSL_CONF, 'something'], []), True),
+    (_msg_files(['what/ever'], [_SSL_CONF]), False),
+))
+@pytest.mark.parametrize('src_maj_ver', ('7', '8', '9'))
+def test_check_openssl(monkeypatch, src_maj_ver, msg, openssl_report):
+    monkeypatch.setattr(reporting, "create_report", create_report_mocked())
+    monkeypatch.setattr(api, 'current_actor', CurrentActorMocked(
+        msgs=[msg],
+        src_ver='{}.6'.format(src_maj_ver),
+        dst_ver='{}.0'.format(int(src_maj_ver) + 1)
+    ))
+    checkopensslconf.process()
+
+    if not openssl_report:
+        assert not reporting.create_report.called, 'OpenSSL report created when it should not.'
+    else:
+        assert reporting.create_report.called, 'OpenSSL report has not been created.'
diff --git a/repos/system_upgrade/common/actors/openssl/migrateopensslconf/actor.py b/repos/system_upgrade/common/actors/openssl/migrateopensslconf/actor.py
new file mode 100644
index 0000000000..16bb3ae0eb
--- /dev/null
+++ b/repos/system_upgrade/common/actors/openssl/migrateopensslconf/actor.py
@@ -0,0 +1,26 @@
+from leapp.actors import Actor
+from leapp.libraries.actor import migrateopensslconf
+from leapp.tags import ApplicationsPhaseTag, IPUWorkflowTag
+
+
+class MigrateOpenSslConf(Actor):
+    """
+    Enforce the target default configuration file to be used.
+
+    If the /etc/pki/tls/openssl.cnf has been modified and openssl.cnf.rpmnew
+    file is created, backup the original one and replace it by the new default.
+
+    tl;dr:
+    if the file is modified; then
+      mv /etc/pki/tls/openssl.cnf{,rpmsave_leapp}
+      mv /etc/pki/tls/openssl.cnf{.rpmnew,}
+    fi
+    """
+
+    name = 'migrate_openssl_conf'
+    consumes = ()
+    produces = ()
+    tags = (IPUWorkflowTag, ApplicationsPhaseTag)
+
+    def process(self):
+        migrateopensslconf.process()
diff --git a/repos/system_upgrade/common/actors/openssl/migrateopensslconf/libraries/migrateopensslconf.py b/repos/system_upgrade/common/actors/openssl/migrateopensslconf/libraries/migrateopensslconf.py
new file mode 100644
index 0000000000..140c57181a
--- /dev/null
+++ b/repos/system_upgrade/common/actors/openssl/migrateopensslconf/libraries/migrateopensslconf.py
@@ -0,0 +1,54 @@
+import os
+
+from leapp.libraries.stdlib import api, CalledProcessError, run
+
+DEFAULT_OPENSSL_CONF = '/etc/pki/tls/openssl.cnf'
+OPENSSL_CONF_RPMNEW = '{}.rpmnew'.format(DEFAULT_OPENSSL_CONF)
+OPENSSL_CONF_BACKUP = '{}.leappsave'.format(DEFAULT_OPENSSL_CONF)
+
+
+def _is_openssl_modified():
+    """
+    Return True if modified in any way
+    """
+    # NOTE(pstodulk): this is different from the approach in scansourcefiles,
+    # where we are interested about modified content. In this case, if the
+    # file is modified in any way, let's do something about that..
+    try:
+        run(['rpm', '-Vf', DEFAULT_OPENSSL_CONF])
+    except CalledProcessError:
+        return True
+    return False
+
+
+def _safe_mv_file(src, dst):
+    """
+    Move the file from src to dst. Return True on success, otherwise False.
+    """
+    try:
+        run(['mv', src, dst])
+    except CalledProcessError:
+        return False
+    return True
+
+
+def process():
+    if not _is_openssl_modified():
+        return
+    if not os.path.exists(OPENSSL_CONF_RPMNEW):
+        api.current_logger().debug('The {} file is modified, but *.rpmsave not found. Cannot do anything.')
+        return
+    if not _safe_mv_file(DEFAULT_OPENSSL_CONF, OPENSSL_CONF_BACKUP):
+        # NOTE(pstodulk): One of reasons could be the file is missing, however
+        # that's not expected to happen at all. If the file is missing before
+        # the upgrade, it will be installed by new openssl* package
+        api.current_logger().error(
+            'Could not back up the {} file. Skipping other actions.'
+            .format(DEFAULT_OPENSSL_CONF)
+        )
+        return
+    if not _safe_mv_file(OPENSSL_CONF_RPMNEW, DEFAULT_OPENSSL_CONF):
+        # unexpected, it's double seatbelt
+        api.current_logger().error('Cannot apply the new openssl configuration file! Restore it from the backup.')
+        if not _safe_mv_file(OPENSSL_CONF_BACKUP, DEFAULT_OPENSSL_CONF):
+            api.current_logger().error('Cannot restore the openssl configuration file!')
diff --git a/repos/system_upgrade/common/actors/scansourcefiles/libraries/scansourcefiles.py b/repos/system_upgrade/common/actors/scansourcefiles/libraries/scansourcefiles.py
index 33e0275fe8..16c0e8aa08 100644
--- a/repos/system_upgrade/common/actors/scansourcefiles/libraries/scansourcefiles.py
+++ b/repos/system_upgrade/common/actors/scansourcefiles/libraries/scansourcefiles.py
@@ -9,6 +9,7 @@
 # '8' (etc..) -> files supposed to be scanned when particular major version of OS is used
 TRACKED_FILES = {
     'common': [
+        '/etc/pki/tls/openssl.cnf',
     ],
     '8': [
     ],