diff --git a/src/specify_cli/extensions.py b/src/specify_cli/extensions.py
index 871503f0ae..172f54718d 100644
--- a/src/specify_cli/extensions.py
+++ b/src/specify_cli/extensions.py
@@ -1112,7 +1112,7 @@ def check_compatibility(
         # Parse version specifier (e.g., ">=0.1.0,<2.0.0")
         try:
             specifier = SpecifierSet(required)
-            if current not in specifier:
+            if not specifier.contains(current, prereleases=True):
                 raise CompatibilityError(
                     f"Extension requires spec-kit {required}, "
                     f"but {speckit_version} is installed.\n"
@@ -1568,7 +1568,7 @@ def version_satisfies(current: str, required: str) -> bool:
     try:
         current_ver = pkg_version.Version(current)
         specifier = SpecifierSet(required)
-        return current_ver in specifier
+        return specifier.contains(current_ver, prereleases=True)
     except (pkg_version.InvalidVersion, InvalidSpecifier):
         return False
 
diff --git a/src/specify_cli/presets.py b/src/specify_cli/presets.py
index c6e75ae790..74c7303ad2 100644
--- a/src/specify_cli/presets.py
+++ b/src/specify_cli/presets.py
@@ -572,7 +572,7 @@ def check_compatibility(
 
         try:
             specifier = SpecifierSet(required)
-            if current not in specifier:
+            if not specifier.contains(current, prereleases=True):
                 raise PresetCompatibilityError(
                     f"Preset requires spec-kit {required}, "
                     f"but {speckit_version} is installed.\n"
diff --git a/tests/test_extensions.py b/tests/test_extensions.py
index 153388a541..9835bee61f 100644
--- a/tests/test_extensions.py
+++ b/tests/test_extensions.py
@@ -750,6 +750,14 @@ def test_check_compatibility_invalid(self, extension_dir, project_dir):
         with pytest.raises(CompatibilityError, match="Extension requires spec-kit"):
             manager.check_compatibility(manifest, "0.0.1")
 
+    def test_check_compatibility_allows_prerelease_builds(self, extension_dir, project_dir):
+        """Prerelease spec-kit builds should satisfy compatible version ranges."""
+        manager = ExtensionManager(project_dir)
+        manifest = ExtensionManifest(extension_dir / "extension.yml")
+
+        result = manager.check_compatibility(manifest, "0.8.8.dev0")
+        assert result is True
+
     def test_install_from_directory(self, extension_dir, project_dir):
         """Test installing extension from directory."""
         manager = ExtensionManager(project_dir)
@@ -1880,6 +1888,10 @@ def test_version_satisfies_complex(self):
         assert version_satisfies("1.0.5", ">=1.0.0,!=1.0.3")
         assert not version_satisfies("1.0.3", ">=1.0.0,!=1.0.3")
 
+    def test_version_satisfies_prerelease(self):
+        """Prerelease builds should satisfy compatible lower bounds."""
+        assert version_satisfies("0.8.8.dev0", ">=0.2.0")
+
     def test_version_satisfies_invalid(self):
         """Test invalid version strings."""
         assert not version_satisfies("invalid", ">=1.0.0")