diff --git a/lib/galaxy/tool_util/deps/container_classes.py b/lib/galaxy/tool_util/deps/container_classes.py
index e89e55ab6b1a..f55f78614f4f 100644
--- a/lib/galaxy/tool_util/deps/container_classes.py
+++ b/lib/galaxy/tool_util/deps/container_classes.py
@@ -16,6 +16,7 @@
 )
 from uuid import uuid4
 
+from packaging.version import Version
 from typing_extensions import Protocol
 
 from galaxy.util import (
@@ -363,7 +364,7 @@ def add_var(name, value):
                 defaults += ",$tool_directory:default_ro"
             if self.job_info.job_directory:
                 defaults += ",$job_directory:default_ro,$job_directory/outputs:rw"
-                if self.tool_info.profile <= 19.09:
+                if Version(str(self.tool_info.profile)) <= Version("19.09"):
                     defaults += ",$job_directory/configs:rw"
             if self.job_info.home_directory is not None:
                 defaults += ",$home_directory:rw"
diff --git a/lib/galaxy/tool_util/linters/general.py b/lib/galaxy/tool_util/linters/general.py
index ee2df7f004d1..d9b06c121725 100644
--- a/lib/galaxy/tool_util/linters/general.py
+++ b/lib/galaxy/tool_util/linters/general.py
@@ -1,6 +1,8 @@
 """This module contains linting functions for general aspects of the tool."""
 import re
 
+from packaging.version import Version
+
 from galaxy.tool_util.version import (
     LegacyVersion,
     parse_version,
@@ -67,7 +69,7 @@ def lint_general(tool_source, lint_ctx):
     profile_valid = PROFILE_PATTERN.match(profile) is not None
     if not profile_valid:
         lint_ctx.error(PROFILE_INVALID_MSG % profile, node=tool_node)
-    elif profile == "16.01":
+    elif Version(profile) == Version("16.01"):
         lint_ctx.valid(PROFILE_INFO_DEFAULT_MSG, node=tool_node)
     else:
         lint_ctx.valid(PROFILE_INFO_SPECIFIED_MSG % profile, node=tool_node)
diff --git a/lib/galaxy/tool_util/linters/inputs.py b/lib/galaxy/tool_util/linters/inputs.py
index 0c619e49095f..7dd46c21f0e9 100644
--- a/lib/galaxy/tool_util/linters/inputs.py
+++ b/lib/galaxy/tool_util/linters/inputs.py
@@ -3,6 +3,8 @@
 import re
 from typing import TYPE_CHECKING
 
+from packaging.version import Version
+
 from galaxy.util import string_as_bool
 from ._util import (
     is_datasource,
@@ -344,7 +346,7 @@ def lint_inputs(tool_source: "ToolSource", lint_ctx: "LintContext"):
         if param_type == "boolean":
             truevalue = param_attrib.get("truevalue", "true")
             falsevalue = param_attrib.get("falsevalue", "false")
-            problematic_booleans_allowed = profile < "23.1"
+            problematic_booleans_allowed = Version(profile) < Version("23.1")
             lint_level = lint_ctx.warn if problematic_booleans_allowed else lint_ctx.error
             if truevalue == falsevalue:
                 lint_level(
diff --git a/lib/galaxy/tool_util/linters/stdio.py b/lib/galaxy/tool_util/linters/stdio.py
index 981882bbde39..ac1171b49eea 100644
--- a/lib/galaxy/tool_util/linters/stdio.py
+++ b/lib/galaxy/tool_util/linters/stdio.py
@@ -1,6 +1,8 @@
 """This module contains a linting functions for tool error detection."""
 import re
 
+from packaging.version import Version
+
 from galaxy.util import etree
 from .command import get_command
 
@@ -20,7 +22,7 @@ def lint_stdio(tool_source, lint_ctx):
     if not stdios:
         command = get_command(tool_xml) if tool_xml else None
         if command is None or not command.get("detect_errors"):
-            if tool_source.parse_profile() <= "16.01":
+            if Version(tool_source.parse_profile()) <= Version("16.01"):
                 lint_ctx.info(
                     "No stdio definition found, tool indicates error conditions with output written to stderr.",
                     node=tool_node,
diff --git a/lib/galaxy/tool_util/parser/xml.py b/lib/galaxy/tool_util/parser/xml.py
index 96b3634c333b..1b7c91755f54 100644
--- a/lib/galaxy/tool_util/parser/xml.py
+++ b/lib/galaxy/tool_util/parser/xml.py
@@ -130,7 +130,7 @@ def __init__(self, xml_tree: ElementTree, source_path=None, macro_paths=None):
         self.root = self.xml_tree.getroot()
         self._source_path = source_path
         self._macro_paths = macro_paths or []
-        self.legacy_defaults = self.parse_profile() == "16.01"
+        self.legacy_defaults = Version(self.parse_profile()) == Version("16.01")
         self._string = xml_to_string(self.root)
 
     def to_string(self):
@@ -250,7 +250,7 @@ def parse_environment_variables(self):
         return environment_variables
 
     def parse_home_target(self):
-        target = "job_home" if self.parse_profile() >= "18.01" else "shared_home"
+        target = "job_home" if Version(self.parse_profile()) >= Version("18.01") else "shared_home"
         command_el = self._command_el
         command_legacy = (command_el is not None) and command_el.get("use_shared_home", None)
         if command_legacy is not None:
@@ -397,7 +397,7 @@ def parse_provided_metadata_style(self):
             style = out_elem.attrib["provided_metadata_style"]
 
         if style is None:
-            style = "legacy" if self.parse_profile() < "17.09" else "default"
+            style = "legacy" if Version(self.parse_profile()) < Version("17.09") else "default"
 
         assert style in ["legacy", "default"]
         return style
@@ -539,7 +539,7 @@ def _parse_output(
         output.filters = data_elem.findall("filter")
         output.tool = tool
         output.from_work_dir = data_elem.get("from_work_dir", None)
-        if output.from_work_dir and getattr(tool, "profile", 0) < 21.09:
+        if output.from_work_dir and Version(str(getattr(tool, "profile", 0))) < Version("21.09"):
             # We started quoting from_work_dir outputs in 21.09.
             # Prior to quoting, trailing spaces had no effect.
             # This ensures that old tools continue to work.
@@ -760,7 +760,7 @@ def __parse_element_tests(parent_element, profile=None):
         element_tests[identifier] = __parse_test_attributes(
             element, element_attrib, parse_elements=True, profile=profile
         )
-        if profile and profile >= "20.09":
+        if profile and Version(profile) >= Version("20.09"):
             element_tests[identifier][1]["expected_sort_order"] = idx
 
     return element_tests
diff --git a/lib/galaxy/tools/__init__.py b/lib/galaxy/tools/__init__.py
index 3168f6a52e13..4f973befaba9 100644
--- a/lib/galaxy/tools/__init__.py
+++ b/lib/galaxy/tools/__init__.py
@@ -913,10 +913,10 @@ def requires_galaxy_python_environment(self):
         if self.tool_type not in ["default", "manage_data", "interactive", "data_source"]:
             return True
 
-        if self.tool_type == "manage_data" and self.profile < 18.09:
+        if self.tool_type == "manage_data" and Version(str(self.profile)) < Version("18.09"):
             return True
 
-        if self.tool_type == "data_source" and self.profile < 21.09:
+        if self.tool_type == "data_source" and Version(str(self.profile)) < Version("21.09"):
             return True
 
         config = self.app.config
@@ -1019,7 +1019,7 @@ def parse(self, tool_source: ToolSource, guid=None, dynamic=False):
         self.python_template_version = tool_source.parse_python_template_version()
         if self.python_template_version is None:
             # If python_template_version not specified we assume tools with profile versions >= 19.05 are python 3 ready
-            if self.profile >= 19.05:
+            if profile >= Version("19.05"):
                 self.python_template_version = Version("3.5")
             else:
                 self.python_template_version = Version("2.7")
@@ -1033,7 +1033,7 @@ def parse(self, tool_source: ToolSource, guid=None, dynamic=False):
 
         self.version = tool_source.parse_version()
         if not self.version:
-            if self.profile < 16.04:
+            if profile < Version("16.04"):
                 # For backward compatibility, some tools may not have versions yet.
                 self.version = "1.0.0"
             else:
diff --git a/lib/galaxy/tools/actions/__init__.py b/lib/galaxy/tools/actions/__init__.py
index cee8b06015d1..54d71b35d995 100644
--- a/lib/galaxy/tools/actions/__init__.py
+++ b/lib/galaxy/tools/actions/__init__.py
@@ -14,6 +14,8 @@
     Union,
 )
 
+from packaging.version import Version
+
 from galaxy import model
 from galaxy.exceptions import ItemAccessibilityException
 from galaxy.job_execution.actions.post import ActionBox
@@ -417,7 +419,7 @@ def execute(
         # format='input" previously would give you a random extension from
         # the input extensions, now it should just give "input" as the output
         # format.
-        input_ext = "data" if tool.profile < 16.04 else "input"
+        input_ext = "data" if Version(str(tool.profile)) < Version("16.04") else "input"
         input_dbkey = incoming.get("dbkey", "?")
         for name, data in reversed(list(inp_data.items())):
             if not data:
@@ -429,7 +431,7 @@ def execute(
                 data = data.to_history_dataset_association(None)
                 inp_data[name] = data
 
-            if tool.profile < 16.04:
+            if Version(str(tool.profile)) < Version("16.04"):
                 input_ext = data.ext
 
             if data.dbkey not in [None, "?"]:
diff --git a/lib/galaxy/tools/evaluation.py b/lib/galaxy/tools/evaluation.py
index d06af3b01d53..a1673450f5f3 100644
--- a/lib/galaxy/tools/evaluation.py
+++ b/lib/galaxy/tools/evaluation.py
@@ -15,6 +15,8 @@
     Union,
 )
 
+from packaging.version import Version
+
 from galaxy import model
 from galaxy.authnz.util import provider_name_to_backend
 from galaxy.job_execution.compute_environment import ComputeEnvironment
@@ -729,7 +731,7 @@ def _build_param_file(self):
         param_dict = self.param_dict
         directory = self.local_working_directory
         command = self.tool.command
-        if self.tool.profile < 16.04 and command and "$param_file" in command:
+        if Version(str(self.tool.profile)) < Version("16.04") and command and "$param_file" in command:
             with tempfile.NamedTemporaryFile(mode="w", dir=directory, delete=False) as param:
                 for key, value in param_dict.items():
                     # parameters can be strings or lists of strings, coerce to list
diff --git a/lib/galaxy/tools/execute.py b/lib/galaxy/tools/execute.py
index 26d29598c740..7c0d8d87701c 100644
--- a/lib/galaxy/tools/execute.py
+++ b/lib/galaxy/tools/execute.py
@@ -17,6 +17,7 @@
 )
 
 from boltons.iterutils import remap
+from packaging.version import Version
 
 from galaxy import model
 from galaxy.exceptions import ToolInputsNotOKException
@@ -310,7 +311,7 @@ def output_name(self, trans, history, params, output):
         return output_collection_name
 
     def sliced_input_collection_structure(self, input_name):
-        unqualified_recurse = self.tool.profile < 18.09 and "|" not in input_name
+        unqualified_recurse = Version(str(self.tool.profile)) < Version("18.09") and "|" not in input_name
 
         def find_collection(input_dict, input_name):
             for key, value in input_dict.items():
diff --git a/lib/galaxy/tools/parameters/basic.py b/lib/galaxy/tools/parameters/basic.py
index ef6a7a19613c..327f3907862c 100644
--- a/lib/galaxy/tools/parameters/basic.py
+++ b/lib/galaxy/tools/parameters/basic.py
@@ -19,6 +19,7 @@
     Union,
 )
 
+from packaging.version import Version
 from webob.compat import cgi_FieldStorage
 
 from galaxy import util
@@ -594,7 +595,7 @@ def __init__(self, tool, input_source):
         super().__init__(tool, input_source)
         truevalue = input_source.get("truevalue", "true")
         falsevalue = input_source.get("falsevalue", "false")
-        if tool and tool.profile >= 23.1:
+        if tool and Version(str(tool.profile)) >= Version("23.1"):
             if truevalue == falsevalue:
                 raise ParameterValueError("Cannot set true and false to the same value", self.name)
             if truevalue.lower() == "false":
@@ -1022,7 +1023,7 @@ def from_json(self, value, trans, other_values=None, require_legal_value=True):
                 "an invalid option (None) was selected, please verify", self.name, None, is_dynamic=self.is_dynamic
             )
         elif not legal_values:
-            if self.optional and self.tool.profile < 18.09:
+            if self.optional and Version(str(self.tool.profile)) < Version("18.09"):
                 # Covers optional parameters with default values that reference other optional parameters.
                 # These will have a value but no legal_values.
                 # See https://github.com/galaxyproject/tools-iuc/pull/1842#issuecomment-394083768 for context.
diff --git a/lib/galaxy/tools/wrappers.py b/lib/galaxy/tools/wrappers.py
index 9e59536c6529..7062cc91b602 100644
--- a/lib/galaxy/tools/wrappers.py
+++ b/lib/galaxy/tools/wrappers.py
@@ -19,6 +19,8 @@
     Union,
 )
 
+from packaging.version import Version
+
 from galaxy.model import (
     DatasetCollection,
     DatasetCollectionElement,
@@ -128,7 +130,7 @@ def __init__(
             and input.type == "text"
             and input.optional
             and input.optionality_inferred
-            and (profile is None or profile < 23.0)
+            and (profile is None or Version(str(profile)) < Version("23.0"))
         ):
             # Tools with old profile versions may treat an optional text parameter as `""`
             value = ""