diff --git a/npm-shrinkwrap.json b/npm-shrinkwrap.json
index ed51c23b..29aee8f3 100644
--- a/npm-shrinkwrap.json
+++ b/npm-shrinkwrap.json
@@ -52,6 +52,7 @@
         "is-root": "^2.1.0",
         "js-yaml": "^4.1.0",
         "JSONStream": "^1.0.3",
+        "jwt-decode": "^3.1.2",
         "livepush": "^3.5.1",
         "lodash": "^4.17.21",
         "mime": "^2.4.6",
@@ -1264,9 +1265,9 @@
       "dev": true
     },
     "node_modules/@babel/parser": {
-      "version": "7.26.1",
-      "resolved": "https://registry.npmjs.org/@babel/parser/-/parser-7.26.1.tgz",
-      "integrity": "sha512-reoQYNiAJreZNsJzyrDNzFQ+IQ5JFiIzAHJg9bn94S3l+4++J7RsIhNMoB+lgP/9tpmiAQqspv+xfdxTSzREOw==",
+      "version": "7.26.2",
+      "resolved": "https://registry.npmjs.org/@babel/parser/-/parser-7.26.2.tgz",
+      "integrity": "sha512-DWMCZH9WA4Maitz2q21SRKHo9QXZxkDsbNZoVD62gusNtNBBqDg9i7uOhASfTfIGNzW+O+r7+jAlM8dwphcJKQ==",
       "dev": true,
       "dependencies": {
         "@babel/types": "^7.26.0"
@@ -1340,12 +1341,12 @@
       }
     },
     "node_modules/@babel/traverse/node_modules/@babel/generator": {
-      "version": "7.26.0",
-      "resolved": "https://registry.npmjs.org/@babel/generator/-/generator-7.26.0.tgz",
-      "integrity": "sha512-/AIkAmInnWwgEAJGQr9vY0c66Mj6kjkE2ZPB1PurTRaRAh3U+J45sAQMjQDJdh4WbR3l0x5xkimXBKyBXXAu2w==",
+      "version": "7.26.2",
+      "resolved": "https://registry.npmjs.org/@babel/generator/-/generator-7.26.2.tgz",
+      "integrity": "sha512-zevQbhbau95nkoxSq3f/DC/SC+EEOUZd3DYqfSkMhY2/wfSeaHV1Ew4vk8e+x8lja31IbyuUa2uQ3JONqKbysw==",
       "dev": true,
       "dependencies": {
-        "@babel/parser": "^7.26.0",
+        "@babel/parser": "^7.26.2",
         "@babel/types": "^7.26.0",
         "@jridgewell/gen-mapping": "^0.3.5",
         "@jridgewell/trace-mapping": "^0.3.25",
@@ -3936,9 +3937,9 @@
       }
     },
     "node_modules/@types/node": {
-      "version": "20.17.2",
-      "resolved": "https://registry.npmjs.org/@types/node/-/node-20.17.2.tgz",
-      "integrity": "sha512-OOHK4sjXqkL7yQ7VEEHcf6+0jSvKjWqwnaCtY7AKD/VLEvRHMsxxu7eI8ErnjxHS8VwmekD4PeVCpu4qZEZSxg==",
+      "version": "20.17.6",
+      "resolved": "https://registry.npmjs.org/@types/node/-/node-20.17.6.tgz",
+      "integrity": "sha512-VEI7OdvK2wP7XHnsuXbAJnEpEkF6NjSN45QJlL4VGqZSXsnicpesdTWsg9RISeSdYd3yeRj/y3k5KGjUXYnFwQ==",
       "dependencies": {
         "undici-types": "~6.19.2"
       }
@@ -5611,9 +5612,9 @@
       }
     },
     "node_modules/balena-sdk/node_modules/@types/node": {
-      "version": "18.19.60",
-      "resolved": "https://registry.npmjs.org/@types/node/-/node-18.19.60.tgz",
-      "integrity": "sha512-cYRj7igVqgxhlHFdBHHpU2SNw3+dN2x0VTZJtLYk6y/ieuGN4XiBgtDjYVktM/yk2y/8pKMileNc6IoEzEJnUw==",
+      "version": "18.19.64",
+      "resolved": "https://registry.npmjs.org/@types/node/-/node-18.19.64.tgz",
+      "integrity": "sha512-955mDqvO2vFf/oL7V3WiUtiz+BugyX8uVbaT2H8oj3+8dRyH2FLiNdowe7eNqRM7IOIZvzDH76EoAT+gwm6aIQ==",
       "dependencies": {
         "undici-types": "~5.26.4"
       }
@@ -17023,10 +17024,9 @@
       }
     },
     "node_modules/tslib": {
-      "version": "2.8.0",
-      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.0.tgz",
-      "integrity": "sha512-jWVzBLplnCmoaTr13V9dYbiQ99wvZRd0vNWaDRg+aVYRcjDF3nDksxFDE/+fkXnKhpnUUkmx5pK/v8mCtLVqZA==",
-      "license": "0BSD"
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
+      "integrity": "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w=="
     },
     "node_modules/tunnel": {
       "version": "0.0.6",
diff --git a/package.json b/package.json
index bfbd53e2..13cfb6f4 100644
--- a/package.json
+++ b/package.json
@@ -231,6 +231,7 @@
     "is-root": "^2.1.0",
     "js-yaml": "^4.1.0",
     "JSONStream": "^1.0.3",
+    "jwt-decode": "^3.1.2",
     "livepush": "^3.5.1",
     "lodash": "^4.17.21",
     "mime": "^2.4.6",
diff --git a/src/commands/api-key/generate.ts b/src/commands/api-key/generate.ts
index 1eb381de..fcdeba0c 100644
--- a/src/commands/api-key/generate.ts
+++ b/src/commands/api-key/generate.ts
@@ -19,6 +19,18 @@ import { Args, Command } from '@oclif/core';
 import { ExpectedError } from '../../errors';
 import { getBalenaSdk, stripIndent } from '../../utils/lazy';
 
+async function isLoggedInWithJwt() {
+	const balena = getBalenaSdk();
+	try {
+		const token = await balena.auth.getToken();
+		const { default: jwtDecode } = await import('jwt-decode');
+		jwtDecode(token);
+		return true;
+	} catch {
+		return false;
+	}
+}
+
 export default class GenerateCmd extends Command {
 	public static description = stripIndent`
 		Generate a new balenaCloud API key.
@@ -48,6 +60,13 @@ export default class GenerateCmd extends Command {
 			key = await getBalenaSdk().models.apiKey.create(params.name);
 		} catch (e) {
 			if (e.name === 'BalenaNotLoggedIn') {
+				if (await isLoggedInWithJwt()) {
+					throw new ExpectedError(stripIndent`
+						This command requires you to have been recently authenticated.
+						Please login again with 'balena login'.
+						In case you are using the Web authorization method, you need to logout and re-login to the dashboard first.
+					`);
+				}
 				throw new ExpectedError(stripIndent`
 					This command cannot be run when logged in with an API key.
 					Please login again with 'balena login' and select an alternative method.