diff --git a/src/api/index.ts b/src/api/index.ts
index 53a80938..2687537e 100644
--- a/src/api/index.ts
+++ b/src/api/index.ts
@@ -8,9 +8,8 @@ import BasicAuthorization, {
   extensionContext,
   workspaceState,
   panel,
-  checkConnection,
+  ensureConnection,
   schemas,
-  checkingConnection,
   inactiveServerIds,
 } from "../extension";
 import { currentWorkspaceFolder, outputChannel, outputConsole } from "../utils";
@@ -121,10 +120,8 @@ export class AtelierAPI {
     return filename;
   }
 
-  public constructor(wsOrFile?: string | vscode.Uri, retryAfter401 = true) {
-    if (retryAfter401) {
-      this.wsOrFile = wsOrFile;
-    }
+  public constructor(wsOrFile?: string | vscode.Uri) {
+    this.wsOrFile = wsOrFile;
     let workspaceFolderName = "";
     let namespace = "";
     if (wsOrFile) {
@@ -328,12 +325,19 @@ export class AtelierAPI {
 
   private async request(
     minVersion: number,
-    method: string,
+    method: "GET" | "HEAD" | "PUT" | "POST" | "DELETE",
     path?: string,
     body?: any,
     params?: any,
     headers?: any,
-    options?: any
+    options?: {
+      /** Abort the request if it hasn't completed within this many milliseconds. */
+      timeout?: number;
+      /** Suppress writing this request/response to the ObjectScript output channel, even when `objectscript.outputRESTTraffic` is on. */
+      noOutput?: boolean;
+      /** On a 401 response, suppress the automatic single retry with fresh credentials. */
+      _retriedAfter401?: boolean;
+    }
   ): Promise<any> {
     const { active, apiVersion, host, port, https } = this.config;
     if (!active || !port || !host) {
@@ -365,7 +369,6 @@ export class AtelierAPI {
       });
       return result.length ? "?" + result.join("&") : "";
     };
-    method = method.toUpperCase();
     if (body && !headers["Content-Type"]) {
       headers["Content-Type"] = "application/json";
     }
@@ -465,7 +468,7 @@ export class AtelierAPI {
       if (response.status === 401) {
         authRequestMap.delete(mapKey);
         cookiesMap.delete(mapKey);
-        if (this.wsOrFile && !checkingConnection) {
+        if (this.wsOrFile) {
           if (!options?._retriedAfter401) {
             return this.request(minVersion, method, originalPath, body, params, headers, {
               ...options,
@@ -473,7 +476,7 @@ export class AtelierAPI {
             });
           }
           setTimeout(() => {
-            checkConnection(
+            ensureConnection(
               this.config.auth.resolved(),
               typeof this.wsOrFile === "object" ? this.wsOrFile : undefined,
               true
@@ -596,9 +599,7 @@ export class AtelierAPI {
         panel.tooltip = "Disconnected";
         workspaceState.update(this.configName.toLowerCase() + ":host", undefined);
         workspaceState.update(this.configName.toLowerCase() + ":port", undefined);
-        if (!checkingConnection) {
-          setTimeout(() => checkConnection(false, undefined, true), 30000);
-        }
+        setTimeout(() => ensureConnection(false, undefined, true), 30000);
       }
       throw error;
     }
diff --git a/src/commands/serverActions.ts b/src/commands/serverActions.ts
index 23176c50..aeec30b1 100644
--- a/src/commands/serverActions.ts
+++ b/src/commands/serverActions.ts
@@ -2,7 +2,7 @@ import * as vscode from "vscode";
 import {
   config,
   workspaceState,
-  checkConnection,
+  ensureConnection,
   explorerProvider,
   filesystemSchemas,
   FILESYSTEM_SCHEMA,
@@ -72,7 +72,7 @@ export async function serverActions(): Promise<void> {
         return connConfig.update("conn", { ...targetConfig, active: !active }, target);
       }
       case "refreshConnection": {
-        await checkConnection(true, undefined, true);
+        await ensureConnection(true, undefined, true);
         break;
       }
       case "switchNamespace": {
diff --git a/src/extension.ts b/src/extension.ts
index f3496d8b..fc4ad561 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -215,8 +215,6 @@ export function config(setting?: string, workspaceFolderName?: string): any {
 
 let reporter: TelemetryReporter | undefined;
 
-export let checkingConnection = false;
-
 export let serverManagerApi: serverManager.ServerManagerAPI;
 
 type ConnSpec = serverManager.IServerSpec & {
@@ -375,18 +373,29 @@ export function getResolvedConnectionSpec(
 /** The `api.serverId`s of all servers that are known to be inactive */
 export const inactiveServerIds: Set<string> = new Set();
 
-export async function checkConnection(
+/** `configName`s for which an `ensureConnection` call is currently in progress */
+const ensuringConnection: Set<string> = new Set();
+
+/**
+ * Verify `uri`'s connection works, repairing it if not (may show a modal credential prompt).
+ * Reflects the outcome in the status bar, `objectscript.conn.active`, and `workspaceState`.
+ * No-ops if a call is already in progress.
+ * @param clearState Discard cached connection details first, forcing fresh resolution.
+ * @param triggerRefreshes Refresh the explorer/projects views once settled.
+ * @param withTimeout Time out the check so it can't hang extension activation.
+ */
+export async function ensureConnection(
   clearState = false,
   uri?: vscode.Uri,
   triggerRefreshes?: boolean,
-  inActivate = false
+  withTimeout = false
 ): Promise<void> {
-  // Do nothing if already checking the connection
-  if (checkingConnection) {
+  const { apiTarget, configName } = connectionTarget(uri);
+  // Do nothing if already checking this connection
+  if (ensuringConnection.has(configName)) {
     return;
   }
 
-  const { apiTarget, configName } = connectionTarget(uri);
   const wsKey = configName.toLowerCase();
   if (clearState) {
     // clean-up cached values
@@ -399,7 +408,7 @@ export async function checkConnection(
     await workspaceState.update(wsKey + ":docker", undefined);
     _onDidChangeConnection.fire();
   }
-  let api = new AtelierAPI(apiTarget, false);
+  let api = new AtelierAPI(apiTarget);
   const { active, host = "", port = 0, superserverPort = 0, ns = "", auth } = api.config;
   vscode.commands.executeCommand("setContext", "vscode-objectscript.connectActive", active);
   if (!panel.text) {
@@ -463,7 +472,7 @@ export async function checkConnection(
   if (api.externalServer) {
     inactiveServerIds.delete(api.serverId);
   }
-  api = new AtelierAPI(apiTarget, false);
+  api = new AtelierAPI(apiTarget);
 
   if (!api.config.host || !api.config.port || !api.config.ns) {
     const message = "'host', 'port' and 'ns' must be specified.";
@@ -474,7 +483,7 @@ export async function checkConnection(
     if (!api.externalServer) await setConnectionState(configName, false);
     return;
   }
-  checkingConnection = true;
+  ensuringConnection.add(configName);
 
   const username = auth.username || "UnknownUser";
   const identity = username.startsWith("*") ? `using ${username.slice(1, -1)}` : `as user \`${username}\``;
@@ -496,7 +505,7 @@ export async function checkConnection(
   // Do the check
   // Only time out requests when called from activate()
   // Timeout is needed in that case to prevent extension activation from hanging
-  const serverInfoTimeout = inActivate ? 5000 : undefined;
+  const serverInfoTimeout = withTimeout ? 5000 : undefined;
   return api
     .serverInfo(true, serverInfoTimeout)
     .then(gotServerInfo)
@@ -524,7 +533,7 @@ export async function checkConnection(
             if (newSpec) {
               // We were able to resolve credentials, so try again
               await workspaceState.update(wsKey + ":password", newSpec.auth?.accessToken);
-              api = new AtelierAPI(apiTarget, false);
+              api = new AtelierAPI(apiTarget);
               await api
                 .serverInfo(true, serverInfoTimeout)
                 .then(async (info) => {
@@ -537,9 +546,6 @@ export async function checkConnection(
                   if (error?.statusCode != 401) errorMessage = undefined;
                   await workspaceState.update(wsKey + ":password", undefined);
                   success = false;
-                })
-                .finally(() => {
-                  checkingConnection = false;
                 });
             }
           } else {
@@ -572,9 +578,6 @@ export async function checkConnection(
                         await workspaceState.update(wsKey + ":password", undefined);
                         return false;
                       })
-                      .finally(() => {
-                        checkingConnection = false;
-                      })
                   );
                 } else {
                   inactiveServerIds.add(api.serverId);
@@ -600,7 +603,7 @@ export async function checkConnection(
       if (!api.externalServer) await setConnectionState(configName, false);
     })
     .finally(() => {
-      checkingConnection = false;
+      ensuringConnection.delete(configName);
       if (triggerRefreshes) {
         setTimeout(() => {
           explorerProvider.refresh();
@@ -948,7 +951,7 @@ export async function activate(context: vscode.ExtensionContext): Promise<server
         // Necessary because we are in our activate method, so its call to the Server Manager API cannot call back to our API to do that.
         await resolveConnectionSpec(serverName, uri);
       } finally {
-        await checkConnection(true, uri, true, true);
+        await ensureConnection(true, uri, true, true);
       }
     } catch (_) {
       // Ignore any failure
@@ -1148,13 +1151,13 @@ export async function activate(context: vscode.ExtensionContext): Promise<server
           await workspaceState.update("workspaceFolder", workspaceFolder);
           // Only need to check when editor is undefined because
           // we will always check when editor is defined below
-          if (!editor) await checkConnection(false);
+          if (!editor) await ensureConnection(false);
         }
       }
       if (editor) {
         const conf = vscode.workspace.getConfiguration("objectscript");
         const uriString = editor.document.uri.toString();
-        await checkConnection(false, editor.document.uri);
+        await ensureConnection(false, editor.document.uri);
         if (
           conf.get("openClassContracted") &&
           editor.document.languageId == clsLangId &&
@@ -1596,9 +1599,9 @@ export async function activate(context: vscode.ExtensionContext): Promise<server
       // This should create new CSP sessions if needed
       for (const wsFolder of affectedWsFolders) {
         try {
-          await checkConnection(true, wsFolder.uri, true);
+          await ensureConnection(true, wsFolder.uri, true);
         } catch {
-          // Errors are handled by checkConnection()
+          // Errors are handled by ensureConnection()
         }
       }
       explorerProvider.refresh();