diff --git a/extensions/git/package.json b/extensions/git/package.json
index 7a9893c47e0..748868778dd 100644
--- a/extensions/git/package.json
+++ b/extensions/git/package.json
@@ -1501,6 +1501,11 @@
           "description": "%config.ignoreMissingGitWarning%",
           "default": false
         },
+        "git.ignoreWindowsGit27Warning": {
+          "type": "boolean",
+          "description": "%config.ignoreWindowsGit27Warning%",
+          "default": false
+        },
         "git.ignoreLimitWarning": {
           "type": "boolean",
           "description": "%config.ignoreLimitWarning%",
diff --git a/extensions/git/package.nls.json b/extensions/git/package.nls.json
index 6b150430b8f..0e8ea1c649e 100644
--- a/extensions/git/package.nls.json
+++ b/extensions/git/package.nls.json
@@ -99,6 +99,7 @@
 	"config.branchWhitespaceChar": "The character to replace whitespace in new branch names.",
 	"config.ignoreLegacyWarning": "Ignores the legacy Git warning.",
 	"config.ignoreMissingGitWarning": "Ignores the warning when Git is missing.",
+	"config.ignoreWindowsGit27Warning": "Ignores the warning when Git 2.25 - 2.26 is installed on Windows.",
 	"config.ignoreLimitWarning": "Ignores the warning when there are too many changes in a repository.",
 	"config.defaultCloneDirectory": "The default location to clone a git repository.",
 	"config.enableSmartCommit": "Commit all changes when there are no staged changes.",
diff --git a/extensions/git/src/main.ts b/extensions/git/src/main.ts
index cabcce04413..8bf85a1b3ee 100644
--- a/extensions/git/src/main.ts
+++ b/extensions/git/src/main.ts
@@ -208,14 +208,25 @@ async function checkGitWindows(info: IGit): Promise<void> {
 		return;
 	}
 
+	const config = workspace.getConfiguration('git');
+	const shouldIgnore = config.get<boolean>('ignoreWindowsGit27Warning') === true;
+
+	if (shouldIgnore) {
+		return;
+	}
+
 	const update = localize('updateGit', "Update Git");
+	const neverShowAgain = localize('neverShowAgain', "Don't Show Again");
 	const choice = await window.showWarningMessage(
 		localize('git2526', "There are known issues with the installed Git {0}. Please update to Git >= 2.27 for the git features to work correctly.", info.version),
-		update
+		update,
+		neverShowAgain
 	);
 
 	if (choice === update) {
 		commands.executeCommand('vscode.open', Uri.parse('https://git-scm.com/'));
+	} else if (choice === neverShowAgain) {
+		await config.update('ignoreWindowsGit27Warning', true, true);
 	}
 }