diff --git a/clearml_agent/backend_api/config/default/agent.conf b/clearml_agent/backend_api/config/default/agent.conf
index 835a3b6..3b979b3 100644
--- a/clearml_agent/backend_api/config/default/agent.conf
+++ b/clearml_agent/backend_api/config/default/agent.conf
@@ -66,7 +66,7 @@
         type: pip,
 
         # specify pip version to use (examples "<20.2", "==19.3.1", "", empty string will install the latest version)
-        pip_version: "<21",
+        pip_version: ["<20.2 ; python_version < '3.10'", "<22.3 ; python_version >= '3.10'"],
         # specify poetry version to use (examples "<2", "==1.1.1", "", empty string will install the latest version)
         # poetry_version: "<2",
 
diff --git a/clearml_agent/commands/worker.py b/clearml_agent/commands/worker.py
index 42e0c3b..c090dc2 100644
--- a/clearml_agent/commands/worker.py
+++ b/clearml_agent/commands/worker.py
@@ -3875,10 +3875,10 @@ class Worker(ServiceCommandSection):
             update_scheme += (
                     docker_bash_script + " ; " +
                     "[ ! -z $LOCAL_PYTHON ] || export LOCAL_PYTHON={python} ; " +
-                    "$LOCAL_PYTHON -m pip install -U \"pip{pip_version}\" ; " +
+                    "$LOCAL_PYTHON -m pip install -U {pip_version} ; " +
                     "$LOCAL_PYTHON -m pip install -U {clearml_agent_wheel} ; ").format(
                 python_single_digit=python_version.split('.')[0],
-                python=python_version, pip_version=PackageManager.get_pip_version(),
+                python=python_version, pip_version=" ".join(PackageManager.get_pip_versions(wrap='\"')),
                 clearml_agent_wheel=clearml_agent_wheel,
                 mount_ssh_ro=mount_ssh_ro, mount_ssh=mount_ssh,
             )
diff --git a/clearml_agent/helper/package/base.py b/clearml_agent/helper/package/base.py
index cfc9a0e..dd6190f 100644
--- a/clearml_agent/helper/package/base.py
+++ b/clearml_agent/helper/package/base.py
@@ -80,7 +80,12 @@ class PackageManager(object):
 
     def upgrade_pip(self):
         result = self._install(
-            select_for_platform(windows='pip{}', linux='pip{}').format(self.get_pip_version()), "--upgrade")
+            *select_for_platform(
+                windows=self.get_pip_versions(),
+                linux=self.get_pip_versions()
+            ),
+            "--upgrade"
+        )
         packages = self.run_with_env(('list',), output=True).splitlines()
         # p.split is ('pip', 'x.y.z')
         pip = [p.split() for p in packages if len(p.split()) == 2 and p.split()[0] == 'pip']
@@ -157,15 +162,26 @@ class PackageManager(object):
     def set_pip_version(cls, version):
         if not version:
             return
-        version = version.replace(' ', '')
-        if ('=' in version) or ('~' in version) or ('<' in version) or ('>' in version):
-            cls._pip_version = version
+
+        if isinstance(version, (list, tuple)):
+            versions = version
         else:
-            cls._pip_version = "=="+version
+            versions = [version]
+
+        cls._pip_version = []
+        for version in versions:
+            version = version.strip()
+            if ('=' in version) or ('~' in version) or ('<' in version) or ('>' in version):
+                cls._pip_version.append(version)
+            else:
+                cls._pip_version.append("==" + version)
 
     @classmethod
-    def get_pip_version(cls):
-        return cls._pip_version or ''
+    def get_pip_versions(cls, pip="pip", wrap='"'):
+        return [
+            (wrap + pip + version + wrap)
+            for version in cls._pip_version or [pip]
+        ]
 
     def get_cached_venv(self, requirements, docker_cmd, python_version, cuda_version, destination_folder):
         # type: (Dict, Optional[Union[dict, str]], Optional[str], Optional[str], Path) -> Optional[Path]
diff --git a/clearml_agent/helper/package/conda_api.py b/clearml_agent/helper/package/conda_api.py
index dd2dee7..9c39a03 100644
--- a/clearml_agent/helper/package/conda_api.py
+++ b/clearml_agent/helper/package/conda_api.py
@@ -135,7 +135,12 @@ class CondaAPI(PackageManager):
         if self.env_read_only:
             print('Conda environment in read-only mode, skipping pip upgrade.')
             return ''
-        return self._install(select_for_platform(windows='pip{}', linux='pip{}').format(self.pip.get_pip_version()))
+        return self._install(
+            *select_for_platform(
+                windows=self.pip.get_pip_versions(),
+                linux=self.pip.get_pip_versions()
+            )
+        )
 
     def create(self):
         """
diff --git a/docs/clearml.conf b/docs/clearml.conf
index f211d25..fdb4b09 100644
--- a/docs/clearml.conf
+++ b/docs/clearml.conf
@@ -79,7 +79,7 @@ agent {
         type: pip,
 
         # specify pip version to use (examples "<20.2", "==19.3.1", "", empty string will install the latest version)
-        # pip_version: "<21"
+        # pip_version: ["<20.2 ; python_version < '3.10'",  "<22.3 ; python_version >= '3.10'"]
         # specify poetry version to use (examples "<2", "==1.1.1", "", empty string will install the latest version)
         # poetry_version: "<2",