diff --git a/LayoutTests/platform/wincairo/TestExpectations b/LayoutTests/platform/wincairo/TestExpectations
index 5f8e821b358c..168c8fcbe181 100644
--- a/LayoutTests/platform/wincairo/TestExpectations
+++ b/LayoutTests/platform/wincairo/TestExpectations
@@ -931,13 +931,66 @@ http/tests/resourceLoadStatistics/ping-to-prevalent-resource.html [ Failure ]
 http/tests/resourceLoadStatistics/standalone-web-application-exempt-from-website-data-deletion.html [ Failure ]
 http/tests/resourceLoadStatistics/third-party-cookie-blocking-on-sites-without-user-interaction.html [ Failure ]
 
-# All timing out
-http/tests/security [ Skip ]
-http/tests/security/401-logout/401-logout.py [ Pass ]
-http/tests/security/cookies/third-party-cookie-blocking.html [ Pass ]
-http/tests/security/cookies/third-party-cookie-blocking-redirect.html [ Pass ]
-http/tests/security/cookies/third-party-cookie-blocking-user-action.html [ Pass ]
-http/tests/security/cookies/third-party-cookie-blocking-xslt.xml [ Pass ]
+http/tests/security/XFrameOptions/x-frame-options-cached.html [ Skip ] # Crash
+http/tests/security/XFrameOptions/x-frame-options-deny.html [ Skip ] # Failure
+http/tests/security/XFrameOptions/x-frame-options-multiple-headers-conflict.html [ Skip ] # Failure
+http/tests/security/XFrameOptions/x-frame-options-multiple-headers-sameorigin-deny.html [ Skip ] # Failure
+http/tests/security/XFrameOptions/x-frame-options-parent-same-origin-deny.html [ Skip ] # Failure
+http/tests/security/anchor-download-allow-data.html [ Skip ] # Crash
+http/tests/security/bypassing-cors-checks-for-extension-urls.html [ Skip ] # Failure
+http/tests/security/canvas-remote-read-remote-video-allowed-anonymous.html [ Skip ] # Failure
+http/tests/security/canvas-remote-read-remote-video-allowed-redirect.html [ Skip ] # Crash
+http/tests/security/canvas-remote-read-remote-video-allowed-with-credentials.html [ Skip ] # Failure
+http/tests/security/canvas-remote-read-remote-video-blocked-no-crossorigin.html [ Skip ] # Crash
+http/tests/security/canvas-remote-read-remote-video-hls.html [ Skip ] # Timeout
+http/tests/security/canvas-remote-read-remote-video-redirect.html [ Skip ] # Crash
+http/tests/security/clipboard/copy-paste-html-across-origin-sanitizes-html.html [ Skip ] # Failure
+http/tests/security/clipboard/copy-paste-html-across-origin-strips-mso-list.html [ Skip ] # Failure
+http/tests/security/clipboard/copy-paste-html-cross-origin-iframe-across-origin.html [ Skip ] # Failure
+http/tests/security/clipboard/copy-paste-html-cross-origin-iframe-in-same-origin.html [ Skip ] # Failure
+http/tests/security/clipboard/copy-paste-url-across-origin-sanitizes-url.html [ Skip ] # Failure
+
+http/tests/security/contentSecurityPolicy [ Skip ] # Failure
+
+http/tests/security/cookie-module-import-propagate.html [ Skip ] # Failure
+http/tests/security/cookie-module-import.html [ Skip ] # Failure
+http/tests/security/cookie-module-propagate.html [ Skip ] # Failure
+http/tests/security/cookie-module.html [ Skip ] # Failure
+http/tests/security/credentials-from-different-domains.html [ Skip ] # Failure
+http/tests/security/credentials-main-resource.html [ Skip ] # Failure
+http/tests/security/cross-frame-access-put.html [ Skip ] # Failure
+http/tests/security/css-mask-image-credentials.html [ Skip ] # ImageOnlyFailure
+http/tests/security/dataTransfer-set-data-file-url.html [ Skip ] # Failure
+http/tests/security/drag-drop-same-unique-origin.html [ Skip ] # Failure
+http/tests/security/drag-over-remote-content-iframe.html [ Skip ] # Failure
+http/tests/security/frame-loading-via-document-write-async-delegates.html [ Skip ] # Failure
+http/tests/security/frame-loading-via-document-write.html [ Skip ] # Failure
+http/tests/security/inactive-document-with-empty-security-origin.html [ Skip ] # Timeout
+http/tests/security/isolatedWorld/cross-origin-xhr.html [ Skip ] # Timeout
+http/tests/security/local-CSS-from-remote.html [ Skip ] # Failure
+http/tests/security/local-JavaScript-from-remote.html [ Skip ] # Failure
+http/tests/security/local-iFrame-from-remote.html [ Skip ] # Failure
+http/tests/security/local-image-from-remote.html [ Skip ] # Failure
+http/tests/security/local-user-CSS-from-remote.html [ Skip ] # Failure
+http/tests/security/local-video-poster-from-remote.html [ Skip ] # Failure
+http/tests/security/local-video-source-from-remote.html [ Skip ] # Failure
+http/tests/security/local-video-src-from-remote.html [ Skip ] # Failure
+http/tests/security/mixedContent/insecure-audio-video-in-main-frame.html [ Skip ] # Failure
+http/tests/security/module-no-mime-type.html [ Skip ] # Failure
+http/tests/security/sync-xhr-partition.html [ Skip ] # Failure
+http/tests/security/video-cross-origin-accessfailure.html [ Skip ] # Failure
+http/tests/security/video-cross-origin-caching.html [ Skip ] # Timeout
+http/tests/security/video-cross-origin-readback.html [ Skip ] # Failure
+http/tests/security/webaudio-render-remote-audio-allowed-crossorigin-redirect.html [ Skip ] # Timeout
+http/tests/security/webaudio-render-remote-audio-allowed-crossorigin.html [ Skip ] # Timeout
+http/tests/security/webaudio-render-remote-audio-blocked-no-crossorigin-redirect.html [ Skip ] # Timeout
+http/tests/security/webaudio-render-remote-audio-blocked-no-crossorigin.html [ Skip ] # Timeout
+http/tests/security/xss-DENIED-xsl-external-entity-redirect.xml [ Skip ] # Failure
+http/tests/security/xss-DENIED-xsl-external-entity.xml [ Skip ] # Failure
+
+webkit.org/b/255747 http/tests/security/canvas-remote-read-remote-video-localhost.html [ Skip ] # Crash
+webkit.org/b/255748 http/tests/security/navigate-when-restoring-cached-page.html [ Skip ] # Crash
+webkit.org/b/255748 http/tests/security/showModalDialog-sync-cross-origin-page-load2.html [ Skip ] # Crash
 
 http/tests/ssl/media-stream [ Skip ]