diff --git a/apps/cli/src/bw.ts b/apps/cli/src/bw.ts
index 753bfe3666..d7ce250a71 100644
--- a/apps/cli/src/bw.ts
+++ b/apps/cli/src/bw.ts
@@ -701,6 +701,8 @@ export class Main {
       this.organizationExportService,
     );
 
+    this.userAutoUnlockKeyService = new UserAutoUnlockKeyService(this.cryptoService);
+
     this.auditService = new AuditService(this.cryptoFunctionService, this.apiService);
     this.program = new Program(this);
     this.vaultProgram = new VaultProgram(this);
@@ -724,8 +726,6 @@ export class Main {
     );
 
     this.providerApiService = new ProviderApiService(this.apiService);
-
-    this.userAutoUnlockKeyService = new UserAutoUnlockKeyService(this.cryptoService);
   }
 
   async run() {
diff --git a/apps/cli/src/program.ts b/apps/cli/src/program.ts
index 5d26b0850e..9664b75776 100644
--- a/apps/cli/src/program.ts
+++ b/apps/cli/src/program.ts
@@ -1,5 +1,6 @@
 import * as chalk from "chalk";
 import { program, Command, OptionValues } from "commander";
+import { firstValueFrom } from "rxjs";
 
 import { AuthenticationStatus } from "@bitwarden/common/auth/enums/authentication-status";
 
@@ -63,8 +64,16 @@ export class Program {
       process.env.BW_NOINTERACTION = "true";
     });
 
-    program.on("option:session", (key) => {
+    program.on("option:session", async (key) => {
       process.env.BW_SESSION = key;
+
+      // once we have the session key, we can set the user key in memory
+      const activeAccount = await firstValueFrom(this.main.accountService.activeAccount$);
+      if (activeAccount) {
+        await this.main.userAutoUnlockKeyService.setUserKeyInMemoryIfAutoUserKeySet(
+          activeAccount.id,
+        );
+      }
     });
 
     program.on("command:*", () => {