diff --git a/Parser/OperatingSystem.php b/Parser/OperatingSystem.php
index 29579231a7..70c78f3265 100644
--- a/Parser/OperatingSystem.php
+++ b/Parser/OperatingSystem.php
@@ -732,7 +732,7 @@ protected function parsePlatform(): string
             return 'SPARC64';
         }
 
-        if ($this->matchUserAgent('64-?bit|WOW64|(?:Intel)?x64|WINDOWS_64|win64|.*amd64|x86_?64')) {
+        if ($this->matchUserAgent('64-?bit|WOW64|(?:Intel)?x64|WINDOWS_64|win64|.*amd64|.*x86_?64')) {
             return 'x64';
         }
 
diff --git a/Tests/Parser/Client/fixtures/library.yml b/Tests/Parser/Client/fixtures/library.yml
index 6bd7012f91..87ae3a0edb 100644
--- a/Tests/Parser/Client/fixtures/library.yml
+++ b/Tests/Parser/Client/fixtures/library.yml
@@ -719,3 +719,15 @@
     type: library
     name: PhantomJS
     version: 2.1.1
+-
+  user_agent: Cygwin-Setup/2.932 (Windows NT 10.0.20348;x86_64;0409;SymLinkPriv)
+  client:
+    type: library
+    name: Cygwin
+    version: "2.932"
+-
+  user_agent: azsdk-python-storage-blob/12.23.0 Python/3.12.5 (Windows-2022Server-10.0.20348-SP0)
+  client:
+    type: library
+    name: Azure Blob Storage
+    version: 12.23.0
diff --git a/Tests/Parser/fixtures/oss.yml b/Tests/Parser/fixtures/oss.yml
index 9f6d3e46bc..7e74c6023f 100644
--- a/Tests/Parser/fixtures/oss.yml
+++ b/Tests/Parser/fixtures/oss.yml
@@ -5733,3 +5733,75 @@
     version: "24"
     platform: ""
     family: Other Mobile
+-
+  user_agent: azsdk-python-storage-blob/12.23.1 Python/3.12.6 (Windows-11-10.0.22631-SP0)
+  os:
+    name: Windows
+    short_name: WIN
+    version: "11"
+    platform: ""
+    family: Windows
+-
+  user_agent: AZURECLI/2.65.0 (MSI) azsdk-python-storage-blob/12.16.0 Python/3.11.8 (Windows-10-10.0.20348-SP0) VSTS_bbc9b9e6-59b6-4cd2-a1a6-91f2e5eb8d58_build_58_0
+  os:
+    name: Windows
+    short_name: WIN
+    version: "10"
+    platform: ""
+    family: Windows
+-
+  user_agent: azsdk-python-storage-blob/12.23.1 Python/3.13.0 (Windows-2025Server-10.0.26100-SP0)
+  os:
+    name: Windows
+    short_name: WIN
+    version: Server 2025
+    platform: ""
+    family: Windows
+-
+  user_agent: azsdk-python-storage-blob/12.23.0 Python/3.12.5 (Windows-2022Server-10.0.20348-SP0)
+  os:
+    name: Windows
+    short_name: WIN
+    version: Server 2022
+    platform: ""
+    family: Windows
+-
+  user_agent: azsdk-python-storage-blob/12.23.1 Python/3.13.0 (Windows-2019Server-10.0.17763-SP0)
+  os:
+    name: Windows
+    short_name: WIN
+    version: Server 2019
+    platform: ""
+    family: Windows
+-
+  user_agent: azsdk-python-storage-blob/12.23.0 Python/3.12.5 (Windows-2016Server-10.0.14393-SP0)
+  os:
+    name: Windows
+    short_name: WIN
+    version: Server 2016
+    platform: ""
+    family: Windows
+-
+  user_agent: azsdk-python-storage-blob/12.17.0 Python/3.12.4 (macOS-14.7-arm64-arm-64bit)
+  os:
+    name: Mac
+    short_name: MAC
+    version: "14.7"
+    platform: ARM
+    family: Mac
+-
+  user_agent: azsdk-python-storage-blob/12.23.1 Python/3.9.20 (Linux-6.5.0-1025-azure-x86_64-with-glibc2.31)
+  os:
+    name: Azure Linux
+    short_name: AZU
+    version: ""
+    platform: x64
+    family: GNU/Linux
+-
+  user_agent: azsdk-python-storage-blob/12.17.0 Python/3.11.10 (Linux-5.15.164.1-1.cm2-x86_64-with-glibc2.31)
+  os:
+    name: Azure Linux
+    short_name: AZU
+    version: "2"
+    platform: x64
+    family: GNU/Linux
diff --git a/regexes/client/libraries.yml b/regexes/client/libraries.yml
index 292f264fa8..150bf4260c 100644
--- a/regexes/client/libraries.yml
+++ b/regexes/client/libraries.yml
@@ -643,3 +643,13 @@
   name: 'ICAP Client'
   version: '$1'
   url: 'https://github.com/Peoplecantfly/icapserver'
+
+- regex: 'Cygwin-Setup(?:/(\d+[.\d]+))?'
+  name: 'Cygwin'
+  version: '$1'
+  url: 'https://www.cygwin.com/'
+
+- regex: 'azsdk-python-storage-blob(?:/(\d+[.\d]+))?'
+  name: 'Azure Blob Storage'
+  version: '$1'
+  url: 'https://learn.microsoft.com/en-us/azure/storage/blobs/storage-quickstart-blobs-python'
diff --git a/regexes/oss.yml b/regexes/oss.yml
index cf93ed43f6..89ecf76453 100644
--- a/regexes/oss.yml
+++ b/regexes/oss.yml
@@ -29,7 +29,11 @@
 ##########
 # Azure Linux (https://github.com/microsoft/azurelinux)
 ##########
-- regex: 'Linux/.+-Microsoft'
+- regex: '.+.cm(\d).x86_64'
+  name: 'Azure Linux'
+  version: '$1'
+
+- regex: 'Linux[/-].+-(azure|Microsoft)'
   name: 'Azure Linux'
   version: ''
 
@@ -1149,6 +1153,10 @@
   name: 'Windows'
   version: '$1'
 
+- regex: 'Windows-(1[01])-'
+  name: 'Windows'
+  version: '$1'
+
 - regex: 'CYGWIN_NT-10\.0|Win(?:dows )?NT 10\.0|Windows[ /]10'
   name: 'Windows'
   version: '10'
@@ -1157,6 +1165,10 @@
   name: 'Windows'
   version: '10'
 
+- regex: 'Windows[/-](2016|2019|2022|2025)Server'
+  name: 'Windows'
+  version: 'Server $1'
+
 - regex: 'Windows/2012ServerR2'
   name: 'Windows'
   version: 'Server 2012 R2'
@@ -1764,7 +1776,7 @@
   name: 'Mac'
   version: '$1'
 
-- regex: '(?:macOS(?:\(Catalyst\))?[ /,]|Mac-)(\d+[.\d]+)'
+- regex: '(?:macOS(?:\(Catalyst\))?[ /,]|Mac(?:os)?-)(\d+[.\d]+)'
   name: 'Mac'
   version: '$1'