diff --git a/server/service/osquery_utils/queries.go b/server/service/osquery_utils/queries.go
index 7ec132f8ad..0e07446036 100644
--- a/server/service/osquery_utils/queries.go
+++ b/server/service/osquery_utils/queries.go
@@ -1770,6 +1770,35 @@ var (
 				s.Version = fmt.Sprintf("%d.%d.%s.%s", yearBasedMajorVersion, yearBasedMinorVersion, "99", eapMinorAndPatchVersion)
 			},
 		},
+		{
+			// Python versions on Windows encode ABI and release information in a way that's incompatible with NVD lookups
+			checkSoftware: func(h *fleet.Host, s *fleet.Software) bool {
+				return s.Source == "programs" && strings.HasPrefix(s.Name, "Python 3.")
+			},
+			mutateSoftware: func(s *fleet.Software, logger log.Logger) {
+				versionComponents := strings.Split(s.Version, ".")
+				patchVersion := versionComponents[2][0 : len(versionComponents[2])-3]
+				releaseLevel := versionComponents[2][len(versionComponents[2])-3 : len(versionComponents[2])-1]
+				releaseSerial := versionComponents[2][len(versionComponents[2])-1 : len(versionComponents[2])]
+
+				candidateSuffix := ""
+				switch releaseLevel { // see https://github.com/python/cpython/issues/100829#issuecomment-1374656643
+				case "10":
+					candidateSuffix = "-alpha" + releaseSerial
+				case "11":
+					candidateSuffix = "-beta" + releaseSerial
+				case "12":
+					candidateSuffix = "-rc" + releaseSerial
+				} // default
+
+				if patchVersion == "" { // dot-zero patch releases have a 3-digit patch + build number
+					patchVersion = "0"
+				}
+
+				versionComponents[2] = patchVersion + candidateSuffix
+				s.Version = strings.Join(versionComponents[0:3], ".")
+			},
+		},
 	}
 )
 
diff --git a/server/service/osquery_utils/queries_test.go b/server/service/osquery_utils/queries_test.go
index a71b1deb80..8292832fd6 100644
--- a/server/service/osquery_utils/queries_test.go
+++ b/server/service/osquery_utils/queries_test.go
@@ -1975,6 +1975,76 @@ func TestSanitizeSoftware(t *testing.T) {
 				BundleIdentifier: "com.jetbrains.intellij-EAP",
 			},
 		},
+		{
+			name: "Python for Windows GA dot-zero",
+			h:    &fleet.Host{},
+			s: &fleet.Software{
+				Name:    "Python 3.12 (64-bit)",
+				Version: "3.12.150.1013",
+				Source:  "programs",
+			},
+			sanitized: &fleet.Software{
+				Name:    "Python 3.12 (64-bit)",
+				Version: "3.12.0",
+				Source:  "programs",
+			},
+		},
+		{
+			name: "Python for Windows GA patch release",
+			h:    &fleet.Host{},
+			s: &fleet.Software{
+				Name:    "Python 3.12.8 (64-bit)",
+				Version: "3.12.8150.0",
+				Source:  "programs",
+			},
+			sanitized: &fleet.Software{
+				Name:    "Python 3.12.8 (64-bit)",
+				Version: "3.12.8",
+				Source:  "programs",
+			},
+		},
+		{
+			name: "Python for Windows alpha",
+			h:    &fleet.Host{},
+			s: &fleet.Software{
+				Name:    "Python 3.14.0a4 (64-bit)",
+				Version: "3.14.104.1013",
+				Source:  "programs",
+			},
+			sanitized: &fleet.Software{
+				Name:    "Python 3.14.0a4 (64-bit)",
+				Version: "3.14.0-alpha4",
+				Source:  "programs",
+			},
+		},
+		{
+			name: "Python for Windows beta",
+			h:    &fleet.Host{},
+			s: &fleet.Software{
+				Name:    "Python 3.14.0b3 (64-bit)",
+				Version: "3.14.113.1013",
+				Source:  "programs",
+			},
+			sanitized: &fleet.Software{
+				Name:    "Python 3.14.0b3 (64-bit)",
+				Version: "3.14.0-beta3",
+				Source:  "programs",
+			},
+		},
+		{
+			name: "Python for Windows RC",
+			h:    &fleet.Host{},
+			s: &fleet.Software{
+				Name:    "Python 3.14.0rc2 (64-bit)",
+				Version: "3.14.122.1013",
+				Source:  "programs",
+			},
+			sanitized: &fleet.Software{
+				Name:    "Python 3.14.0rc2 (64-bit)",
+				Version: "3.14.0-rc2",
+				Source:  "programs",
+			},
+		},
 	} {
 		t.Run(tc.name, func(t *testing.T) {
 			sanitizeSoftware(tc.h, tc.s, log.NewNopLogger())
diff --git a/server/vulnerabilities/nvd/cpe_test.go b/server/vulnerabilities/nvd/cpe_test.go
index 8a669d81c9..380aa89c48 100644
--- a/server/vulnerabilities/nvd/cpe_test.go
+++ b/server/vulnerabilities/nvd/cpe_test.go
@@ -894,10 +894,19 @@ func TestCPEFromSoftwareIntegration(t *testing.T) {
 			software: fleet.Software{
 				Name:             "Python 3.10.6 (64-bit)",
 				Source:           "programs",
-				Version:          "3.10.6150.0",
+				Version:          "3.10.6",
 				Vendor:           "Python Software Foundation",
 				BundleIdentifier: "",
-			}, cpe: "cpe:2.3:a:python:python:3.10.6150.0:*:*:*:*:windows:*:*",
+			}, cpe: "cpe:2.3:a:python:python:3.10.6:*:*:*:*:windows:*:*",
+		},
+		{
+			software: fleet.Software{
+				Name:    "Python 3.14.0a1 (64-bit)",
+				Source:  "programs",
+				Version: "3.14.0-alpha1",
+				Vendor:  "Python Software Foundation",
+				// should be "cpe:2.3:a:python:python:3.14.0:alpha1:*:*:*:windows:*:*"; see #24810
+			}, cpe: "cpe:2.3:a:python:python:3.14.0-alpha1:*:*:*:*:windows:*:*",
 		},
 		{
 			software: fleet.Software{
diff --git a/server/vulnerabilities/nvd/cpe_translations.json b/server/vulnerabilities/nvd/cpe_translations.json
index 00ea56732d..ee81548e5c 100644
--- a/server/vulnerabilities/nvd/cpe_translations.json
+++ b/server/vulnerabilities/nvd/cpe_translations.json
@@ -70,6 +70,16 @@
       "vendor": ["7-zip"]
     }
   },
+  {
+    "software": {
+      "name": ["/^Python 3\\.\\d{1,2}/"],
+      "source": ["programs"]
+    },
+    "filter": {
+      "product": ["python"],
+      "vendor": ["python"]
+    }
+  },
   {
     "software": {
       "name": ["Docs"],