diff --git a/extensions/typescript-language-features/src/features/completions.ts b/extensions/typescript-language-features/src/features/completions.ts
index c6cf96b752f..d82457554c6 100644
--- a/extensions/typescript-language-features/src/features/completions.ts
+++ b/extensions/typescript-language-features/src/features/completions.ts
@@ -350,7 +350,7 @@ class TypeScriptCompletionItemProvider implements vscode.CompletionItemProvider
 	private getTsTriggerCharacter(context: vscode.CompletionContext): Proto.CompletionsTriggerCharacter | undefined {
 		// Workaround for https://github.com/Microsoft/TypeScript/issues/27321
 		if (context.triggerCharacter === '@'
-			&& this.client.apiVersion.gte(API.v310) && !this.client.apiVersion.gte(API.v320)
+			&& this.client.apiVersion.gte(API.v310) && this.client.apiVersion.lt(API.v320)
 		) {
 			return undefined;
 		}
@@ -480,7 +480,7 @@ class TypeScriptCompletionItemProvider implements vscode.CompletionItemProvider
 		line: vscode.TextLine,
 		position: vscode.Position
 	): boolean {
-		if (context.triggerCharacter && !this.client.apiVersion.gte(API.v290)) {
+		if (context.triggerCharacter && this.client.apiVersion.lt(API.v290)) {
 			if ((context.triggerCharacter === '"' || context.triggerCharacter === '\'')) {
 				// make sure we are in something that looks like the start of an import
 				const pre = line.text.slice(0, position.character);
diff --git a/extensions/typescript-language-features/src/features/fileConfigurationManager.ts b/extensions/typescript-language-features/src/features/fileConfigurationManager.ts
index 1dd92934879..043a6009ab5 100644
--- a/extensions/typescript-language-features/src/features/fileConfigurationManager.ts
+++ b/extensions/typescript-language-features/src/features/fileConfigurationManager.ts
@@ -176,7 +176,7 @@ export default class FileConfigurationManager {
 	}
 
 	private getPreferences(document: vscode.TextDocument): Proto.UserPreferences {
-		if (!this.client.apiVersion.gte(API.v290)) {
+		if (this.client.apiVersion.lt(API.v290)) {
 			return {};
 		}
 
diff --git a/extensions/typescript-language-features/src/features/quickFix.ts b/extensions/typescript-language-features/src/features/quickFix.ts
index d81cc2ff961..1dd8135adda 100644
--- a/extensions/typescript-language-features/src/features/quickFix.ts
+++ b/extensions/typescript-language-features/src/features/quickFix.ts
@@ -282,7 +282,7 @@ class TypeScriptQuickFixProvider implements vscode.CodeActionProvider {
 		diagnostic: vscode.Diagnostic,
 		tsAction: Proto.CodeFixAction,
 	): CodeActionSet {
-		if (!tsAction.fixId || !this.client.apiVersion.gte(API.v270) || results.hasFixAllAction(results)) {
+		if (!tsAction.fixId || this.client.apiVersion.lt(API.v270) || results.hasFixAllAction(results)) {
 			return results;
 		}
 
diff --git a/extensions/typescript-language-features/src/features/updatePathsOnRename.ts b/extensions/typescript-language-features/src/features/updatePathsOnRename.ts
index 457c04090eb..b1793ffb420 100644
--- a/extensions/typescript-language-features/src/features/updatePathsOnRename.ts
+++ b/extensions/typescript-language-features/src/features/updatePathsOnRename.ts
@@ -81,7 +81,7 @@ class UpdateImportsOnFileRenameHandler {
 		this.client.bufferSyncSupport.closeResource(targetResource);
 		this.client.bufferSyncSupport.openTextDocument(document);
 
-		if (!this.client.apiVersion.gte(API.v300) && !fs.lstatSync(newResource.fsPath).isDirectory()) {
+		if (this.client.apiVersion.lt(API.v300) && !fs.lstatSync(newResource.fsPath).isDirectory()) {
 			// Workaround for https://github.com/Microsoft/vscode/issues/52967
 			// Never attempt to update import paths if the file does not contain something the looks like an export
 			try {
@@ -253,7 +253,7 @@ class UpdateImportsOnFileRenameHandler {
 		const edits: Proto.FileCodeEdits[] = [];
 		for (const edit of response.body) {
 			// Workaround for https://github.com/Microsoft/vscode/issues/52675
-			if (!this.client.apiVersion.gte(API.v300)) {
+			if (this.client.apiVersion.lt(API.v300)) {
 				if ((edit as Proto.FileCodeEdits).fileName.match(/[\/\\]node_modules[\/\\]/gi)) {
 					continue;
 				}
diff --git a/extensions/typescript-language-features/src/typeScriptServiceClientHost.ts b/extensions/typescript-language-features/src/typeScriptServiceClientHost.ts
index 3de0b7054e0..df5613d849a 100644
--- a/extensions/typescript-language-features/src/typeScriptServiceClientHost.ts
+++ b/extensions/typescript-language-features/src/typeScriptServiceClientHost.ts
@@ -103,7 +103,7 @@ export default class TypeScriptServiceClientHost extends Disposable {
 
 		this.client.ensureServiceStarted();
 		this.client.onReady(() => {
-			if (!this.client.apiVersion.gte(API.v230)) {
+			if (this.client.apiVersion.lt(API.v230)) {
 				return;
 			}
 
diff --git a/extensions/typescript-language-features/src/typescriptServiceClient.ts b/extensions/typescript-language-features/src/typescriptServiceClient.ts
index 57d81c1e954..73745af9dba 100644
--- a/extensions/typescript-language-features/src/typescriptServiceClient.ts
+++ b/extensions/typescript-language-features/src/typescriptServiceClient.ts
@@ -350,7 +350,7 @@ export default class TypeScriptServiceClient extends Disposable implements IType
 	}
 
 	public async openTsServerLogFile(): Promise<boolean> {
-		if (!this.apiVersion.gte(API.v222)) {
+		if (this.apiVersion.lt(API.v222)) {
 			vscode.window.showErrorMessage(
 				localize(
 					'typescript.openTsServerLog.notSupported',
@@ -409,7 +409,7 @@ export default class TypeScriptServiceClient extends Disposable implements IType
 	}
 
 	private setCompilerOptionsForInferredProjects(configuration: TypeScriptServiceConfiguration): void {
-		if (!this.apiVersion.gte(API.v206)) {
+		if (this.apiVersion.lt(API.v206)) {
 			return;
 		}
 
diff --git a/extensions/typescript-language-features/src/utils/api.ts b/extensions/typescript-language-features/src/utils/api.ts
index 18c8c0b94cc..9bcab14cf59 100644
--- a/extensions/typescript-language-features/src/utils/api.ts
+++ b/extensions/typescript-language-features/src/utils/api.ts
@@ -56,4 +56,8 @@ export default class API {
 	public gte(other: API): boolean {
 		return semver.gte(this.version, other.version);
 	}
+
+	public lt(other: API): boolean {
+		return !this.gte(other);
+	}
 }
\ No newline at end of file