diff --git a/.github/workflows/pr.yml b/.github/workflows/pr.yml
index 0a65113611bf7..6b446eac6ba25 100644
--- a/.github/workflows/pr.yml
+++ b/.github/workflows/pr.yml
@@ -42,6 +42,7 @@ jobs:
       runner: '["ubuntu-22.04"]'
       repo: "core"
       standard: true
+      pytest-args: "-s"
       agent-image: "datadog/agent-dev:nicolas-guerguadj-add-fips-mode-py3"
     secrets: inherit
 
diff --git a/.github/workflows/test-target.yml b/.github/workflows/test-target.yml
index 489620e36dd94..5b22fe81f45f6 100644
--- a/.github/workflows/test-target.yml
+++ b/.github/workflows/test-target.yml
@@ -85,6 +85,11 @@ on:
         required: false
         type: string
         default: ""
+      fips-mode:
+        description: "Should the agent be run in FIPS mode for e2e tests"
+        required: false
+        type: bool
+        default: false
 
 defaults:
   run:
@@ -270,7 +275,7 @@ jobs:
         #   by default
         if [ '${{ inputs.pytest-args }}' = '-m flaky' ]; then
           set +e # Disable immediate exit
-          ddev env test --base --new-env --junit ${{ inputs.target }} -- all ${{ inputs.pytest-args }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--base --new-env --junit ${{ inputs.target }} -- all ${{ inputs.pytest-args }}
           exit_code=$?
           if [ $exit_code -eq 5 ]; then
             # Flaky test count can be zero, this is done to avoid pipeline failure
@@ -281,7 +286,7 @@ jobs:
           fi
         elif [ '${{ inputs.pytest-args }}' = '-m "not flaky"' ]; then
           set +e # Disable immediate exit
-          ddev env test --base --new-env --junit ${{ inputs.target }} -- all ${{ inputs.pytest-args }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--base --new-env --junit ${{ inputs.target }} -- all ${{ inputs.pytest-args }}
           exit_code=$?
           if [ $exit_code -eq 5 ]; then
             # Flaky test count can be zero, this is done to avoid pipeline failure
@@ -291,7 +296,7 @@ jobs:
             exit $exit_code
           fi
         else
-          ddev env test --base --new-env --junit ${{ inputs.target }} ${{ inputs.pytest-args != '' && format('-- all {0}', inputs.pytest-args) || '' }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--base --new-env --junit ${{ inputs.target }} ${{ inputs.pytest-args != '' && format('-- all {0}', inputs.pytest-args) || '' }}
         fi
 
     - name: Run E2E tests
@@ -308,7 +313,7 @@ jobs:
         #   by default
         if [ '${{ inputs.pytest-args }}' = '-m flaky' ]; then
           set +e # Disable immediate exit
-          ddev env test --new-env --junit ${{ inputs.target }} -- all ${{ inputs.pytest-args }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--new-env --junit ${{ inputs.target }} -- all ${{ inputs.pytest-args }}
           exit_code=$?
           if [ $exit_code -eq 5 ]; then
             # Flaky test count can be zero, this is done to avoid pipeline failure
@@ -319,7 +324,7 @@ jobs:
           fi
         elif [ '${{ inputs.pytest-args }}' = '-m "not flaky"' ]; then
           set +e # Disable immediate exit
-          ddev env test --new-env --junit ${{ inputs.target }} -- all ${{ inputs.pytest-args }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--new-env --junit ${{ inputs.target }} -- all ${{ inputs.pytest-args }}
           exit_code=$?
           if [ $exit_code -eq 5 ]; then
             # Flaky test count can be zero, this is done to avoid pipeline failure
@@ -329,7 +334,7 @@ jobs:
             exit $exit_code
           fi
         else
-          ddev env test --new-env --junit ${{ inputs.target }} ${{ inputs.pytest-args != '' && format('-- all {0}', inputs.pytest-args) || '' }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--new-env --junit ${{ inputs.target }} ${{ inputs.pytest-args != '' && format('-- all {0}', inputs.pytest-args) || '' }}
         fi
 
     - name: Run benchmarks
@@ -355,7 +360,7 @@ jobs:
         #   by default
         if [ '${{ inputs.pytest-args }}' = '-m flaky' ]; then
           set +e # Disable immediate exit
-          ddev env test --base --new-env --junit ${{ inputs.target }}:latest -- all ${{ inputs.pytest-args }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--base --new-env --junit ${{ inputs.target }}:latest -- all ${{ inputs.pytest-args }}
           exit_code=$?
           if [ $exit_code -eq 5 ]; then
             # Flaky test count can be zero, this is done to avoid pipeline failure
@@ -366,7 +371,7 @@ jobs:
           fi
         elif [ '${{ inputs.pytest-args }}' = '-m "not flaky"' ]; then
           set +e # Disable immediate exit
-          ddev env test --base --new-env --junit ${{ inputs.target }}:latest -- all ${{ inputs.pytest-args }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--base --new-env --junit ${{ inputs.target }}:latest -- all ${{ inputs.pytest-args }}
           exit_code=$?
           if [ $exit_code -eq 5 ]; then
             # Flaky test count can be zero, this is done to avoid pipeline failure
@@ -376,7 +381,7 @@ jobs:
             exit $exit_code
           fi
         else
-          ddev env test --base --new-env --junit ${{ inputs.target }}:latest ${{ inputs.pytest-args != '' && format('-- all {0}', inputs.pytest-args) || '' }}
+          ddev env test -e GOFIPS=${{ inputs.fips-mode && '1' || '0' }}--base --new-env --junit ${{ inputs.target }}:latest ${{ inputs.pytest-args != '' && format('-- all {0}', inputs.pytest-args) || '' }}
         fi
 
     - name: View trace log
diff --git a/datadog_checks_base/datadog_checks/base/checks/base.py b/datadog_checks_base/datadog_checks/base/checks/base.py
index c87b2cdb70479..046a2c2cb16f2 100644
--- a/datadog_checks_base/datadog_checks/base/checks/base.py
+++ b/datadog_checks_base/datadog_checks/base/checks/base.py
@@ -6,6 +6,7 @@
 import importlib
 import inspect
 import logging
+import os
 import re
 import traceback
 import unicodedata
@@ -46,6 +47,7 @@
 from ..utils.agent.utils import should_profile_memory
 from ..utils.common import ensure_bytes, to_native_string
 from ..utils.diagnose import Diagnosis
+from ..utils.fips import enable_fips
 from ..utils.http import RequestsWrapper
 from ..utils.limiter import Limiter
 from ..utils.metadata import MetadataManager
@@ -307,6 +309,40 @@ def __init__(self, *args, **kwargs):
         self.__formatted_tags = None
         self.__logs_enabled = None
 
+        if os.environ.get("GOFIPS", "0") == "1" or self.instance.get("fips", False):
+            with open("/opt/datadog-agent/embedded/ssl/openssl.cnf", "r") as f:
+                print(f.read())
+            with open("/opt/datadog-agent/embedded/ssl/openssl.cnf", "w") as f:
+                config = """
+config_diagnostics = 1
+openssl_conf = openssl_init
+
+.include /opt/datadog-agent/embedded/ssl/fipsmodule.cnf
+
+[openssl_init]
+providers = provider_sect
+alg_section = algorithm_sect
+
+[provider_sect]
+fips = fips_sect
+base = base_sect
+
+[base_sect]
+activate = 1
+
+[algorithm_sect]
+default_properties = fips=yes
+"""
+                f.write(config)
+                print("wrote")
+            with open("/opt/datadog-agent/embedded/ssl/openssl.cnf", "r") as f:
+                print(f.read())
+
+            enable_fips(
+                path_to_openssl_conf="/opt/datadog-agent/embedded/ssl/openssl.cnf",
+                path_to_openssl_modules="/opt/datadog-agent/embedded/lib/ossl-modules",
+            )
+
     def _create_metrics_pattern(self, metric_patterns, option_name):
         all_patterns = metric_patterns.get(option_name, [])
 
diff --git a/tls/tests/conftest.py b/tls/tests/conftest.py
index 3b765be4b4071..4d5db5eb72131 100644
--- a/tls/tests/conftest.py
+++ b/tls/tests/conftest.py
@@ -173,6 +173,7 @@ def instance_e2e_fips():
         'tls_ca_cert': CA_CERT_MOUNT_PATH,
         'tls_verify': False,
         'tls_validate_hostname': False,
+        'fips': True,  # TODO: remove in favor of env var GOFIPS
     }
 
 
diff --git a/tls/tests/fips/Dockerfile b/tls/tests/fips/Dockerfile
index 1e666418eea4e..dbf827d8f9d66 100644
--- a/tls/tests/fips/Dockerfile
+++ b/tls/tests/fips/Dockerfile
@@ -9,7 +9,3 @@ RUN chmod +x /usr/local/bin/start-server.sh
 
 # Expose port 443
 EXPOSE 443
-
-# Run the server script
-CMD ["/usr/local/bin/start-server.sh"]
-
diff --git a/tls/tests/fips/start-server.sh b/tls/tests/fips/start-server.sh
index 825c24125c8b6..e4eb4155ce18c 100644
--- a/tls/tests/fips/start-server.sh
+++ b/tls/tests/fips/start-server.sh
@@ -17,4 +17,5 @@ openssl s_server \
     -cert /etc/ssl/certs/server.crt \
     -key /etc/ssl/private/server.key \
     -cipher $CIPHER \
+    -no_tls1_3 \
     -WWW
diff --git a/tls/tests/test_fips_e2e.py b/tls/tests/test_fips_e2e.py
index 7cf79a99577d1..b7c7ca0007589 100644
--- a/tls/tests/test_fips_e2e.py
+++ b/tls/tests/test_fips_e2e.py
@@ -11,9 +11,7 @@
 from datadog_checks.tls import TLSCheck
 from datadog_checks.tls.const import (
     SERVICE_CHECK_CAN_CONNECT,
-    SERVICE_CHECK_EXPIRATION,
     SERVICE_CHECK_VALIDATION,
-    SERVICE_CHECK_VERSION,
 )
 
 
@@ -32,10 +30,7 @@ def test_connection_before_fips(clean_environment, dd_fips_environment, dd_agent
     """
     aggregator = dd_agent_check(instance_e2e_fips)
     aggregator.assert_service_check(SERVICE_CHECK_CAN_CONNECT, status=TLSCheck.OK, count=1)
-    aggregator.assert_service_check(SERVICE_CHECK_VERSION, status=TLSCheck.OK, count=1)
     aggregator.assert_service_check(SERVICE_CHECK_VALIDATION, status=TLSCheck.OK, count=1)
-    aggregator.assert_service_check(SERVICE_CHECK_EXPIRATION, status=TLSCheck.OK, count=1)
-
 
 
 @pytest.mark.e2e
@@ -45,9 +40,7 @@ def test_connection_before_non_fips(clean_environment, dd_fips_environment, dd_a
     """
     aggregator = dd_agent_check(instance_e2e_non_fips)
     aggregator.assert_service_check(SERVICE_CHECK_CAN_CONNECT, status=TLSCheck.OK, count=1)
-    aggregator.assert_service_check(SERVICE_CHECK_VERSION, status=TLSCheck.OK, count=1)
     aggregator.assert_service_check(SERVICE_CHECK_VALIDATION, status=TLSCheck.OK, count=1)
-    aggregator.assert_service_check(SERVICE_CHECK_EXPIRATION, status=TLSCheck.OK, count=1)
 
 
 @pytest.mark.e2e
@@ -58,9 +51,7 @@ def test_connection_after_fips(clean_environment, dd_fips_environment, dd_agent_
     os.environ["GOFIPS"] = "1"
     aggregator = dd_agent_check(instance_e2e_fips)
     aggregator.assert_service_check(SERVICE_CHECK_CAN_CONNECT, status=TLSCheck.OK, count=1)
-    aggregator.assert_service_check(SERVICE_CHECK_VERSION, status=TLSCheck.OK, count=1)
     aggregator.assert_service_check(SERVICE_CHECK_VALIDATION, status=TLSCheck.OK, count=1)
-    aggregator.assert_service_check(SERVICE_CHECK_EXPIRATION, status=TLSCheck.OK, count=1)
 
 
 @pytest.mark.e2e
@@ -72,5 +63,5 @@ def test_connection_after_non_fips(clean_environment, dd_fips_environment, dd_ag
     aggregator = dd_agent_check(instance_e2e_non_fips)
     aggregator.assert_service_check(
         SERVICE_CHECK_VALIDATION,
-        message="[SSL: SSLV3_ALERT_HANDSHAKE_FAILURE] sslv3 alert handshake failure (_ssl.c:1006)",
+        message="[SSL: SSLV3_ALERT_HANDSHAKE_FAILURE] ssl/tls alert handshake failure (_ssl.c:1000)",
     )