diff --git a/.github/workflows/check.yaml b/.github/workflows/check.yaml
index 68120bde6..f796b324f 100644
--- a/.github/workflows/check.yaml
+++ b/.github/workflows/check.yaml
@@ -55,6 +55,10 @@ jobs:
         uses: actions/checkout@v4
         with:
           fetch-depth: 0
+      - name: 🏷️ Fetch upstream tags for versioning
+        shell: bash
+        run: |
+          git fetch --force --tags https://github.com/pypa/virtualenv.git
       - name: 🐍 Setup Python for tox
         uses: actions/setup-python@v5
         with:
@@ -63,9 +67,9 @@ jobs:
         shell: bash
         run: |
           if [[ "${{ matrix.py }}" == "3.13t" || "${{ matrix.py }}" == "3.14t" ]]; then
-            uv tool install --no-managed-python --python 3.14 tox --with .
+            uv tool install --no-managed-python --python 3.14 "tox>=4.32" --with .
           else
-            uv tool install --no-managed-python --python 3.14 tox --with tox-uv --with .
+            uv tool install --no-managed-python --python 3.14 "tox>=4.32" --with tox-uv --with .
           fi
       - name: 🐍 Setup Python for test ${{ matrix.py }}
         uses: actions/setup-python@v5
@@ -106,7 +110,7 @@ jobs:
           echo "TOXENV=$py" >> "$GITHUB_ENV"
           echo "Set TOXENV=$py"
       - name: 🏗️ Setup test suite
-        run: tox run -vvvv --notest --skip-missing-interpreters false
+        run: tox run -vvvv --notest --skip-missing-interpreters
       - name: 🏃 Run test suite
         run: tox run --skip-pkg-install
         timeout-minutes: 20
@@ -137,12 +141,16 @@ jobs:
       - name: 🚀 Install uv
         uses: astral-sh/setup-uv@v4
       - name: 📦 Install tox
-        run: uv tool install --python-preference only-managed --python 3.14 tox --with tox-uv
+        run: uv tool install --python-preference only-managed --python 3.14 "tox>=4.32" --with tox-uv
       - name: 📥 Checkout code
         uses: actions/checkout@v4
         with:
           fetch-depth: 0
+      - name: 🏷️ Fetch upstream tags for versioning
+        shell: bash
+        run: |
+          git fetch --force --tags https://github.com/pypa/virtualenv.git
       - name: 🏗️ Setup check suite
-        run: tox run -vv --notest --skip-missing-interpreters false -e ${{ matrix.tox_env }}
+        run: tox run -vv --notest --skip-missing-interpreters -e ${{ matrix.tox_env }}
       - name: 🏃 Run check for ${{ matrix.tox_env }}
-        run: tox run --skip-pkg-install -e ${{ matrix.tox_env }}
+        run: tox run --skip-pkg-install -e ${{ matrix.tox_env }}
\ No newline at end of file
diff --git a/src/virtualenv/discovery/builtin.py b/src/virtualenv/discovery/builtin.py
index e2d193911..ed0829471 100644
--- a/src/virtualenv/discovery/builtin.py
+++ b/src/virtualenv/discovery/builtin.py
@@ -46,8 +46,9 @@ def add_parser_arguments(cls, parser: ArgumentParser) -> None:
             type=str,
             action="append",
             default=[],
-            help="interpreter based on what to create environment (path/identifier) "
-            "- by default use the interpreter where the tool is installed - first found wins",
+            help="interpreter based on what to create environment (path/identifier/version-specifier)"
+            "- by default use the interpreter where the tool is installed - first found wins."
+            "Version specifiers (e.g., >=3.12, ~=3.11.0, ==3.10) are also supported",
         )
         parser.add_argument(
             "--try-first-with",
diff --git a/src/virtualenv/discovery/py_info.py b/src/virtualenv/discovery/py_info.py
index c2310cd7e..f077c0694 100644
--- a/src/virtualenv/discovery/py_info.py
+++ b/src/virtualenv/discovery/py_info.py
@@ -393,27 +393,49 @@ def clear_cache(cls, app_data):
         clear(app_data)
         cls._cache_exe_discovery.clear()
 
-    def satisfies(self, spec, impl_must_match):  # noqa: C901, PLR0911
+    def _check_path_match(self, spec):
+        """Check if path specification matches. Returns None if no path check needed."""
+        if not spec.path:
+            return None
+        if self.executable == os.path.abspath(spec.path):
+            return True
+        if spec.is_abs:
+            return False
+        # if path set, and is not our original executable name, this does not match
+        basename = os.path.basename(self.original_executable)
+        spec_path = spec.path
+        if sys.platform == "win32":
+            basename, suffix = os.path.splitext(basename)
+            if spec_path.endswith(suffix):
+                spec_path = spec_path[: -len(suffix)]
+        return basename == spec_path
+
+    def _check_impl_match(self, spec, impl_must_match):
+        """Check if implementation matches."""
+        return (
+            not impl_must_match
+            or spec.implementation is None
+            or spec.implementation.lower() == self.implementation.lower()
+        )
+
+    def _check_version_match(self, spec):
+        """Check if version matches spec (handles both specifiers and exact versions)."""
+        if spec.version_specifier is not None:
+            version_string = f"{self.version_info.major}.{self.version_info.minor}.{self.version_info.micro}"
+            return version_string in spec.version_specifier
+        # Check exact version match (backward compatibility)
+        for our, req in zip(self.version_info[0:3], (spec.major, spec.minor, spec.micro)):
+            if req is not None and our is not None and our != req:
+                return False
+        return True
+
+    def satisfies(self, spec, impl_must_match):
         """Check if a given specification can be satisfied by the this python interpreter instance."""
-        if spec.path:
-            if self.executable == os.path.abspath(spec.path):
-                return True  # if the path is a our own executable path we're done
-            if not spec.is_abs:
-                # if path set, and is not our original executable name, this does not match
-                basename = os.path.basename(self.original_executable)
-                spec_path = spec.path
-                if sys.platform == "win32":
-                    basename, suffix = os.path.splitext(basename)
-                    if spec_path.endswith(suffix):
-                        spec_path = spec_path[: -len(suffix)]
-                if basename != spec_path:
-                    return False
-
-        if (
-            impl_must_match
-            and spec.implementation is not None
-            and spec.implementation.lower() != self.implementation.lower()
-        ):
+        path_match = self._check_path_match(spec)
+        if path_match is False:
+            return False
+
+        if not self._check_impl_match(spec, impl_must_match):
             return False
 
         if spec.architecture is not None and spec.architecture != self.architecture:
@@ -422,10 +444,7 @@ def satisfies(self, spec, impl_must_match):  # noqa: C901, PLR0911
         if spec.free_threaded is not None and spec.free_threaded != self.free_threaded:
             return False
 
-        for our, req in zip(self.version_info[0:3], (spec.major, spec.minor, spec.micro)):
-            if req is not None and our is not None and our != req:
-                return False
-        return True
+        return self._check_version_match(spec)
 
     _current_system = None
     _current = None
diff --git a/src/virtualenv/discovery/py_spec.py b/src/virtualenv/discovery/py_spec.py
index d8519c23d..392e160b8 100644
--- a/src/virtualenv/discovery/py_spec.py
+++ b/src/virtualenv/discovery/py_spec.py
@@ -5,6 +5,8 @@
 import os
 import re
 
+from packaging.specifiers import InvalidSpecifier, SpecifierSet
+
 PATTERN = re.compile(r"^(?P<impl>[a-zA-Z]+)?(?P<version>[0-9.]+)?(?P<threaded>t)?(?:-(?P<arch>32|64))?$")
 
 
@@ -22,6 +24,7 @@ def __init__(  # noqa: PLR0913
         path: str | None,
         *,
         free_threaded: bool | None = None,
+        version_specifier: SpecifierSet | None = None,
     ) -> None:
         self.str_spec = str_spec
         self.implementation = implementation
@@ -31,13 +34,29 @@ def __init__(  # noqa: PLR0913
         self.free_threaded = free_threaded
         self.architecture = architecture
         self.path = path
+        self.version_specifier = version_specifier
 
     @classmethod
     def from_string_spec(cls, string_spec: str):  # noqa: C901, PLR0912
         impl, major, minor, micro, threaded, arch, path = None, None, None, None, None, None, None
+        version_specifier = None
+
+        # Check if this looks like a version specifier (contains comparison operators)
+        # Version specifiers start with >=, <=, ==, ~=, !=, >, <, or ===
+        specifier_operators = (">=", "<=", "==", "~=", "!=", ">", "<", "===")
+        is_specifier = any(string_spec.lstrip().startswith(op) for op in specifier_operators)
+
+        if is_specifier:
+            try:
+                version_specifier = SpecifierSet(string_spec)
+                # Extract the base version from the specifier for display purposes
+                # We'll match any version that satisfies the specifier
+            except InvalidSpecifier:  # If it fails to parse as a specifier, treat it as a regular spec
+                is_specifier = False
+
         if os.path.isabs(string_spec):  # noqa: PLR1702
             path = string_spec
-        else:
+        elif not is_specifier:
             ok = False
             match = re.match(PATTERN, string_spec)
             if match:
@@ -74,7 +93,17 @@ def _int_or_none(val):
             if not ok:
                 path = string_spec
 
-        return cls(string_spec, impl, major, minor, micro, arch, path, free_threaded=threaded)
+        return cls(
+            string_spec,
+            impl,
+            major,
+            minor,
+            micro,
+            arch,
+            path,
+            free_threaded=threaded,
+            version_specifier=version_specifier,
+        )
 
     def generate_re(self, *, windows: bool) -> re.Pattern:
         """Generate a regular expression for matching against a filename."""
@@ -120,7 +149,16 @@ def satisfies(self, spec):
 
     def __repr__(self) -> str:
         name = type(self).__name__
-        params = "implementation", "major", "minor", "micro", "architecture", "path", "free_threaded"
+        params = (
+            "implementation",
+            "major",
+            "minor",
+            "micro",
+            "architecture",
+            "path",
+            "free_threaded",
+            "version_specifier",
+        )
         return f"{name}({', '.join(f'{k}={getattr(self, k)}' for k in params if getattr(self, k) is not None)})"