diff --git a/CHANGELOG.md b/CHANGELOG.md
index cb708eccd..efbbfaa0b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,7 +3,8 @@
 ### New Features & Improvements
 
 * Changed `lando setup` to pull common plugins based on release `channel` to better mimic fatcore
-* Rebased `axios` on `@npmcli/agent` to improve request consistency across environments
+* Improved internet detection tests [#243](https://github.com/lando/core/issues/243)
+* Rebased `axios` and `octokit`  on `@npmcli/agent` to improve request consistency across environments
 * Updated default Docker Desktop version to `4.34.3`
 * Updated default Docker Engine version to `27.3.1`
 * Udpated recommended Docker Destkop range to `>=4.34.0`
@@ -19,6 +20,7 @@
 * Added `debugShim` to `lando.utils`
 * Added `downloadX` to `lando.utils`
 * Added `getAxios` to `lando.utils`
+* Added `getOctokit` to `lando.utils`
 * Added `getUserShell` to `lando.utils`
 * Added `getUserShellProfile` to `lando.utils`
 * Added `isVersionLte` to `lando.utils`
diff --git a/components/plugin.js b/components/plugin.js
index 87e62ec24..b1b5e5867 100644
--- a/components/plugin.js
+++ b/components/plugin.js
@@ -292,11 +292,6 @@ class Plugin {
     const channel = this.channel === 'stable' ? 'latest' : this.channel;
 
     try {
-      // check internet connection
-      const online = await require('is-online')();
-      // throw error if not online
-      if (!online) throw new Error('Cannot detect connection to internet!');
-      // process to check
       // get release data
       const data = await packument(this.spec, merge({}, [Plugin.config, {fullMetadata: true}]));
       // build a list of highest available versions
diff --git a/hooks/lando-setup-build-engine-darwin.js b/hooks/lando-setup-build-engine-darwin.js
index 86642c09a..5d2414d17 100644
--- a/hooks/lando-setup-build-engine-darwin.js
+++ b/hooks/lando-setup-build-engine-darwin.js
@@ -1,5 +1,6 @@
 'use strict';
 
+const axios = require('../utils/get-axios')();
 const os = require('os');
 const path = require('path');
 const semver = require('semver');
@@ -86,6 +87,9 @@ module.exports = async (lando, options) => {
   // cosmetics
   const install = version ? `v${version}` : `build ${build}`;
 
+  // download url
+  const url = getEngineDownloadUrl(build);
+
   // darwin install task
   options.tasks.push({
     title: `Downloading build engine`,
@@ -112,8 +116,8 @@ module.exports = async (lando, options) => {
     canRun: async () => {
       // throw if we cannot resolve a semantic version to a buildid
       if (!build) throw new Error(`Could not resolve ${install} to an installable version!`);
-      // throw error if not online
-      if (!await require('is-online')()) throw new Error('Cannot detect connection to internet!');
+      // throw error if we cannot ping the download link
+      await axios.head(url);
       // throw if user is not an admin
       if (!await require('../utils/is-admin-user')()) {
         throw new Error([
@@ -127,7 +131,7 @@ module.exports = async (lando, options) => {
     task: async (ctx, task) => {
       try {
         // download the installer
-        ctx.download = await downloadDockerDesktop(getEngineDownloadUrl(build), {ctx, debug, task});
+        ctx.download = await downloadDockerDesktop(url, {ctx, debug, task});
 
         // prompt for password if interactive
         if (ctx.password === undefined && lando.config.isInteractive) {
diff --git a/hooks/lando-setup-build-engine-linux.js b/hooks/lando-setup-build-engine-linux.js
index 666a6ce43..1fdbd4bcd 100644
--- a/hooks/lando-setup-build-engine-linux.js
+++ b/hooks/lando-setup-build-engine-linux.js
@@ -1,5 +1,6 @@
 'use strict';
 
+const axios = require('../utils/get-axios')();
 const os = require('os');
 const path = require('path');
 
@@ -31,6 +32,7 @@ module.exports = async (lando, options) => {
   if (options.buildEngine === false) return;
 
   const version = options.buildEngine;
+  const url = 'https://get.docker.com';
 
   // darwin install task
   options.tasks.push({
@@ -46,8 +48,8 @@ module.exports = async (lando, options) => {
     canRun: async () => {
       // throw if we cannot resolve a semantic version to a buildid
       if (!version) throw new Error(`Could not resolve ${version} to an installable version!`);
-      // throw error if not online
-      if (!await require('is-online')()) throw new Error('Cannot detect connection to internet!');
+      // throw error if we cannot ping the download link
+      await axios.head(url);
       // throw if user is not an admin
       if (!await require('../utils/is-admin-user')()) {
         throw new Error([
@@ -61,7 +63,7 @@ module.exports = async (lando, options) => {
     task: async (ctx, task) => {
       try {
         // download the installer
-        ctx.download = await downloadDockerEngine('https://get.docker.com', {ctx, debug, task});
+        ctx.download = await downloadDockerEngine(url, {ctx, debug, task});
 
         // prompt for password if interactive and we dont have it
         if (ctx.password === undefined && lando.config.isInteractive) {
diff --git a/hooks/lando-setup-build-engine-win32.js b/hooks/lando-setup-build-engine-win32.js
index bb188cb86..73ea717a8 100644
--- a/hooks/lando-setup-build-engine-win32.js
+++ b/hooks/lando-setup-build-engine-win32.js
@@ -1,5 +1,6 @@
 'use strict';
 
+const axios = require('../utils/get-axios')();
 const os = require('os');
 const path = require('path');
 const semver = require('semver');
@@ -90,10 +91,13 @@ module.exports = async (lando, options) => {
   // get stuff from config/opts
   const build = getId(options.buildEngine);
   const version = getVersion(options.buildEngine);
+
   // cosmetics
   const buildEngine = process.platform === 'linux' ? 'docker-engine' : 'docker-desktop';
   const install = version ? `v${version}` : `build ${build}`;
 
+  const url = getEngineDownloadUrl(build);
+
   // win32 install docker desktop task
   options.tasks.push({
     title: `Downloading build engine`,
@@ -120,8 +124,8 @@ module.exports = async (lando, options) => {
     canRun: async () => {
       // throw if we cannot resolve a semantic version to a buildid
       if (!build) throw new Error(`Could not resolve ${install} to an installable version!`);
-      // throw error if not online
-      if (!await require('is-online')()) throw new Error('Cannot detect connection to internet!');
+      // throw error if we cannot ping the download link
+      await axios.head(url);
       // @TODO: check for wsl2?
       return true;
     },
@@ -135,7 +139,7 @@ module.exports = async (lando, options) => {
     task: async (ctx, task) => {
       try {
         // download the installer
-        ctx.download = await downloadDockerDesktop(getEngineDownloadUrl(build), {ctx, debug, task});
+        ctx.download = await downloadDockerDesktop(url, {ctx, debug, task});
         // script
         const script = [path.join(lando.config.userConfRoot, 'scripts', 'install-docker-desktop.ps1')];
         // args
diff --git a/hooks/lando-setup-install-ca-linux.js b/hooks/lando-setup-install-ca-linux.js
index e3cb65634..891ccec07 100644
--- a/hooks/lando-setup-install-ca-linux.js
+++ b/hooks/lando-setup-install-ca-linux.js
@@ -40,8 +40,6 @@ module.exports = async (lando, options) => {
       }
     },
     canRun: async () => {
-      // Check for internet connection
-      if (!await require('is-online')()) throw new Error('Cannot detect connection to internet!');
       // Check for admin privileges
       if (!await require('../utils/is-admin-user')()) {
         throw new Error([
diff --git a/hooks/lando-setup-orchestrator.js b/hooks/lando-setup-orchestrator.js
index d4ce69ef9..1bb8b468e 100644
--- a/hooks/lando-setup-orchestrator.js
+++ b/hooks/lando-setup-orchestrator.js
@@ -1,5 +1,6 @@
 'use strict';
 
+const axios = require('../utils/get-axios')();
 const fs = require('fs');
 const path = require('path');
 
@@ -64,10 +65,9 @@ module.exports = async (lando, options) => {
       return !!orchestratorBin && typeof orchestrator === 'string' && fs.existsSync(dest);
     },
     canRun: async () => {
-      const online = await require('is-online')();
-      // throw error if not online
-      if (!online) throw new Error('Cannot detect connection to internet!');
-
+      // throw error if we cannot ping the download link
+      await axios.head(url);
+      // true if we get here
       return true;
     },
     task: async (ctx, task) => new Promise((resolve, reject) => {
diff --git a/lib/lando.js b/lib/lando.js
index 865450efb..4ab2bed8a 100644
--- a/lib/lando.js
+++ b/lib/lando.js
@@ -273,6 +273,7 @@ module.exports = class Lando {
 
     // updater is more complex now
     this.updates = new UpdateManager({
+      agent: this.config.userAgent,
       channel: this.config.channel,
       cli: _.get(this, 'config.cli'),
       config: getPluginConfig(this.config.pluginConfigFile, this.config.pluginConfig),
diff --git a/lib/updates.js b/lib/updates.js
index 9ea076fba..8ace61653 100644
--- a/lib/updates.js
+++ b/lib/updates.js
@@ -1,14 +1,15 @@
 'use strict';
 
+const axios = require('../utils/get-axios')();
 const fs = require('fs');
 const get = require('lodash/get');
+const getOctokit = require('../utils/get-octokit');
 const os = require('os');
 const path = require('path');
 const semver = require('semver');
 const uniqBy = require('lodash/uniqBy');
 
 const {color} = require('listr2');
-const {Octokit} = require('@octokit/rest');
 
 const getOS = () => {
   switch (process.platform) {
@@ -32,6 +33,7 @@ const getPluginClass = ({channel, config, debug} = {}) => {
 
 module.exports = class UpdateManager {
   constructor({
+    agent = 'Lando',
     config = {},
     cli,
     channel = 'stable',
@@ -40,6 +42,7 @@ module.exports = class UpdateManager {
     plugins = [],
   } = {}) {
     // set things
+    this.agent = agent;
     this._plugins = plugins;
     this.channel = channel;
     this.cli = cli;
@@ -108,11 +111,7 @@ module.exports = class UpdateManager {
 
       checks.push(new Promise(async resolve => {
         // summon the katkraken
-        const octokit = new Octokit({auth: get(process, 'env.LANDO_GITHUB_TOKEN')});
-        // check internet connection
-        const online = await require('is-online')();
-        // throw error if not online
-        if (!online) throw new Error('Cannot detect connection to internet!');
+        const octokit = getOctokit({auth: get(process, 'env.LANDO_GITHUB_TOKEN'), userAgent: this.agent});
         // just a helper to give consistent prez
         const extra = color.dim('@lando/cli');
 
@@ -230,8 +229,8 @@ module.exports = class UpdateManager {
             throw new Error(`Lando cannot write to ${this._cli.installPath}!`);
           }
 
-          // throw error if not online
-          if (!await require('is-online')()) throw new Error('Cannot detect connection to internet!');
+          // throw error if we cannot ping the download link
+          await axios.head(this._cli.update.download);
 
           // or true
           return true;
@@ -320,7 +319,7 @@ module.exports = class UpdateManager {
     });
 
     // summon the katkraken
-    const octokit = new Octokit({auth: get(process, 'env.LANDO_GITHUB_TOKEN')});
+    const octokit = getOctokit({auth: get(process, 'env.LANDO_GITHUB_TOKEN'), userAgent: this.agent});
 
     // get latest
     try {
diff --git a/lib/utils.js b/lib/utils.js
index e40766a3d..fc0aff969 100644
--- a/lib/utils.js
+++ b/lib/utils.js
@@ -110,6 +110,7 @@ module.exports = {
   debugShim: (...args) => require('../utils/debug-shim')(...args),
   downloadX: (...args) => require('../utils/download-x')(...args),
   getAxios: (...args) => require('../utils/get-axios')(...args),
+  getOctokit: (...args) => require('../utils/get-octokit')(...args),
   getUserShell: (...args) => require('../utils/get-user-shell')(...args),
   getUserShellProfile: (...args) => require('../utils/get-user-shell-profile')(...args),
   isVersionLte: (...args) => require('../utils/is-lte-version')(...args),
diff --git a/package-lock.json b/package-lock.json
index e11f388dc..bb2f5c74d 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -37,7 +37,6 @@
         "is-class": "^0.0.9",
         "is-docker": "^2.2.1",
         "is-interactive": "^1",
-        "is-online": "^9",
         "is-root": "^2",
         "js-yaml": "^4.1.0",
         "jsonfile": "^2.4.0",
@@ -1886,12 +1885,6 @@
         "node": ">=12"
       }
     },
-    "node_modules/@leichtgewicht/ip-codec": {
-      "version": "2.0.5",
-      "resolved": "https://registry.npmjs.org/@leichtgewicht/ip-codec/-/ip-codec-2.0.5.tgz",
-      "integrity": "sha512-Vo+PSpZG2/fmgmiNzYK9qWRh8h/CHrwD0mo1h1DzL4yzHNSfWYujGTYsWGreD000gcgmZ7K4Ys6Tx9TxtsKdDw==",
-      "license": "MIT"
-    },
     "node_modules/@nicolo-ribaudo/eslint-scope-5-internals": {
       "version": "5.1.1-v1",
       "resolved": "https://registry.npmjs.org/@nicolo-ribaudo/eslint-scope-5-internals/-/eslint-scope-5-internals-5.1.1-v1.tgz",
@@ -3603,18 +3596,6 @@
         "node": "^14.17.0 || ^16.13.0 || >=18.0.0"
       }
     },
-    "node_modules/@sindresorhus/is": {
-      "version": "4.6.0",
-      "resolved": "https://registry.npmjs.org/@sindresorhus/is/-/is-4.6.0.tgz",
-      "integrity": "sha512-t09vSN3MdfsyCHoFcTRCH/iUtG7OJ0CsjzB8cjAmKc/va/kIgeDI/TxsigdncE/4be734m0cvIYwNaV4i2XqAw==",
-      "license": "MIT",
-      "engines": {
-        "node": ">=10"
-      },
-      "funding": {
-        "url": "https://github.com/sindresorhus/is?sponsor=1"
-      }
-    },
     "node_modules/@sinonjs/commons": {
       "version": "1.8.6",
       "resolved": "https://registry.npmjs.org/@sinonjs/commons/-/commons-1.8.6.tgz",
@@ -3664,18 +3645,6 @@
       "dev": true,
       "license": "(Unlicense OR Apache-2.0)"
     },
-    "node_modules/@szmarczak/http-timer": {
-      "version": "4.0.6",
-      "resolved": "https://registry.npmjs.org/@szmarczak/http-timer/-/http-timer-4.0.6.tgz",
-      "integrity": "sha512-4BAffykYOgO+5nzBWYwE3W90sBgLJoUPRWWcL8wlyiM8IB8ipJz3UMJ9KXQd1RKQXpKp8Tutn80HZtWsu2u76w==",
-      "license": "MIT",
-      "dependencies": {
-        "defer-to-connect": "^2.0.0"
-      },
-      "engines": {
-        "node": ">=10"
-      }
-    },
     "node_modules/@tootallnate/once": {
       "version": "2.0.0",
       "resolved": "https://registry.npmjs.org/@tootallnate/once/-/once-2.0.0.tgz",
@@ -3707,18 +3676,6 @@
         "node": "^14.17.0 || ^16.13.0 || >=18.0.0"
       }
     },
-    "node_modules/@types/cacheable-request": {
-      "version": "6.0.3",
-      "resolved": "https://registry.npmjs.org/@types/cacheable-request/-/cacheable-request-6.0.3.tgz",
-      "integrity": "sha512-IQ3EbTzGxIigb1I3qPZc1rWJnH0BmSKv5QYTalEwweFvyBDLSAe24zP0le/hyi7ecGfZVlIVAg4BZqb8WBwKqw==",
-      "license": "MIT",
-      "dependencies": {
-        "@types/http-cache-semantics": "*",
-        "@types/keyv": "^3.1.4",
-        "@types/node": "*",
-        "@types/responselike": "^1.0.0"
-      }
-    },
     "node_modules/@types/cli-progress": {
       "version": "3.11.6",
       "resolved": "https://registry.npmjs.org/@types/cli-progress/-/cli-progress-3.11.6.tgz",
@@ -3745,21 +3702,6 @@
         "@types/unist": "*"
       }
     },
-    "node_modules/@types/http-cache-semantics": {
-      "version": "4.0.4",
-      "resolved": "https://registry.npmjs.org/@types/http-cache-semantics/-/http-cache-semantics-4.0.4.tgz",
-      "integrity": "sha512-1m0bIFVc7eJWyve9S0RnuRgcQqF/Xd5QsUZAZeQFr1Q3/p9JWoQQEqmVy+DPTNpGXwhgIetAoYF8JSc33q29QA==",
-      "license": "MIT"
-    },
-    "node_modules/@types/keyv": {
-      "version": "3.1.4",
-      "resolved": "https://registry.npmjs.org/@types/keyv/-/keyv-3.1.4.tgz",
-      "integrity": "sha512-BQ5aZNSCpj7D6K2ksrRCTmKRLEpnPvWDiLPfoGyhZ++8YtiK9d/3DBKPJgry359X/P1PfruyYwvnvwFjuEiEIg==",
-      "license": "MIT",
-      "dependencies": {
-        "@types/node": "*"
-      }
-    },
     "node_modules/@types/linkify-it": {
       "version": "5.0.0",
       "resolved": "https://registry.npmjs.org/@types/linkify-it/-/linkify-it-5.0.0.tgz",
@@ -3825,15 +3767,6 @@
       "dev": true,
       "license": "MIT"
     },
-    "node_modules/@types/responselike": {
-      "version": "1.0.3",
-      "resolved": "https://registry.npmjs.org/@types/responselike/-/responselike-1.0.3.tgz",
-      "integrity": "sha512-H/+L+UkTV33uf49PH5pCAUBVPNj2nDBXTN+qS1dOwyyg24l3CcicicCA7ca+HMvJBZcFgl5r8e+RR6elsb4Lyw==",
-      "license": "MIT",
-      "dependencies": {
-        "@types/node": "*"
-      }
-    },
     "node_modules/@types/unist": {
       "version": "3.0.3",
       "resolved": "https://registry.npmjs.org/@types/unist/-/unist-3.0.3.tgz",
@@ -4976,33 +4909,6 @@
         "node": ">=12"
       }
     },
-    "node_modules/cacheable-lookup": {
-      "version": "5.0.4",
-      "resolved": "https://registry.npmjs.org/cacheable-lookup/-/cacheable-lookup-5.0.4.tgz",
-      "integrity": "sha512-2/kNscPhpcxrOigMZzbiWF7dz8ilhb/nIHU3EyZiXWXpeq/au8qJ8VhdftMkty3n7Gj6HIGalQG8oiBNB3AJgA==",
-      "license": "MIT",
-      "engines": {
-        "node": ">=10.6.0"
-      }
-    },
-    "node_modules/cacheable-request": {
-      "version": "7.0.4",
-      "resolved": "https://registry.npmjs.org/cacheable-request/-/cacheable-request-7.0.4.tgz",
-      "integrity": "sha512-v+p6ongsrp0yTGbJXjgxPow2+DL93DASP4kXCDKb8/bwRtt9OEF3whggkkDkGNzgcWy2XaF4a8nZglC7uElscg==",
-      "license": "MIT",
-      "dependencies": {
-        "clone-response": "^1.0.2",
-        "get-stream": "^5.1.0",
-        "http-cache-semantics": "^4.0.0",
-        "keyv": "^4.0.0",
-        "lowercase-keys": "^2.0.0",
-        "normalize-url": "^6.0.1",
-        "responselike": "^2.0.0"
-      },
-      "engines": {
-        "node": ">=8"
-      }
-    },
     "node_modules/caching-transform": {
       "version": "4.0.0",
       "resolved": "https://registry.npmjs.org/caching-transform/-/caching-transform-4.0.0.tgz",
@@ -5471,18 +5377,6 @@
         "node": ">=0.8"
       }
     },
-    "node_modules/clone-response": {
-      "version": "1.0.3",
-      "resolved": "https://registry.npmjs.org/clone-response/-/clone-response-1.0.3.tgz",
-      "integrity": "sha512-ROoL94jJH2dUVML2Y/5PEDNaSHgeOdSDicUyS7izcF63G6sTc/FTjLub4b8Il9S8S0beOfYt0TaA5qvFK+w0wA==",
-      "license": "MIT",
-      "dependencies": {
-        "mimic-response": "^1.0.0"
-      },
-      "funding": {
-        "url": "https://github.com/sponsors/sindresorhus"
-      }
-    },
     "node_modules/cmd-shim": {
       "version": "6.0.3",
       "resolved": "https://registry.npmjs.org/cmd-shim/-/cmd-shim-6.0.3.tgz",
@@ -5834,6 +5728,7 @@
       "version": "6.0.0",
       "resolved": "https://registry.npmjs.org/decompress-response/-/decompress-response-6.0.0.tgz",
       "integrity": "sha512-aW35yZM6Bb/4oJlZncMH2LCoZtJXTRxES17vE3hoRiowU2kWHaJKFkSBDnDR+cm9J+9QhXmREyIfv0pji9ejCQ==",
+      "dev": true,
       "license": "MIT",
       "dependencies": {
         "mimic-response": "^3.1.0"
@@ -5849,6 +5744,7 @@
       "version": "3.1.0",
       "resolved": "https://registry.npmjs.org/mimic-response/-/mimic-response-3.1.0.tgz",
       "integrity": "sha512-z0yWI+4FDrrweS8Zmt4Ej5HdJmky15+L2e6Wgn3+iK5fWzb6T3fhNFq2+MeTRb064c6Wr4N/wv0DzQTjNzHNGQ==",
+      "dev": true,
       "license": "MIT",
       "engines": {
         "node": ">=10"
@@ -5903,15 +5799,6 @@
         "url": "https://github.com/sponsors/sindresorhus"
       }
     },
-    "node_modules/defer-to-connect": {
-      "version": "2.0.1",
-      "resolved": "https://registry.npmjs.org/defer-to-connect/-/defer-to-connect-2.0.1.tgz",
-      "integrity": "sha512-4tvttepXG1VaYGrRibk5EwJd1t4udunSOVMdLSAL6mId1ix438oPwPZMALY41FCijukO1L0twNcGsdzS7dHgDg==",
-      "license": "MIT",
-      "engines": {
-        "node": ">=10"
-      }
-    },
     "node_modules/delay": {
       "version": "5.0.0",
       "resolved": "https://registry.npmjs.org/delay/-/delay-5.0.0.tgz",
@@ -6011,30 +5898,6 @@
         "node": ">=8"
       }
     },
-    "node_modules/dns-packet": {
-      "version": "5.6.1",
-      "resolved": "https://registry.npmjs.org/dns-packet/-/dns-packet-5.6.1.tgz",
-      "integrity": "sha512-l4gcSouhcgIKRvyy99RNVOgxXiicE+2jZoNmaNmZ6JXiGajBOJAesk1OBlJuM5k2c+eudGdLxDqXuPCKIj6kpw==",
-      "license": "MIT",
-      "dependencies": {
-        "@leichtgewicht/ip-codec": "^2.0.1"
-      },
-      "engines": {
-        "node": ">=6"
-      }
-    },
-    "node_modules/dns-socket": {
-      "version": "4.2.2",
-      "resolved": "https://registry.npmjs.org/dns-socket/-/dns-socket-4.2.2.tgz",
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-      }
-    },
-    "node_modules/public-ip/node_modules/p-cancelable": {
-      "version": "1.1.0",
-      "resolved": "https://registry.npmjs.org/p-cancelable/-/p-cancelable-1.1.0.tgz",
-      "integrity": "sha512-s73XxOZ4zpt1edZYZzvhqFa6uvQc1vwUa0K0BdtIZgQMAJj9IbebH+JkgKZc9h+B05PKHLOTl4ajG1BmNrVZlw==",
-      "license": "MIT",
-      "engines": {
-        "node": ">=6"
-      }
-    },
-    "node_modules/public-ip/node_modules/responselike": {
-      "version": "1.0.2",
-      "resolved": "https://registry.npmjs.org/responselike/-/responselike-1.0.2.tgz",
-      "integrity": "sha512-/Fpe5guzJk1gPqdJLJR5u7eG/gNY4nImjbRDaVWVMRhne55TCmj2i9Q+54PBRfatRC8v/rIiv9BN0pMd9OV5EQ==",
-      "license": "MIT",
-      "dependencies": {
-        "lowercase-keys": "^1.0.0"
-      }
-    },
-    "node_modules/public-ip/node_modules/responselike/node_modules/lowercase-keys": {
-      "version": "1.0.1",
-      "resolved": "https://registry.npmjs.org/lowercase-keys/-/lowercase-keys-1.0.1.tgz",
-      "integrity": "sha512-G2Lj61tXDnVFFOi8VZds+SoQjtQC3dgokKdDG2mTm1tx4m50NUHBOZSBwQQHyy0V12A0JTG4icfZQH+xPyh8VA==",
-      "license": "MIT",
-      "engines": {
-        "node": ">=0.10.0"
-      }
-    },
     "node_modules/pump": {
       "version": "3.0.2",
       "resolved": "https://registry.npmjs.org/pump/-/pump-3.0.2.tgz",
       "integrity": "sha512-tUPXtzlGM8FE3P0ZL6DVs/3P58k9nk8/jZeQCurTJylQA8qFYzHFfhBJkuqyE0FifOsQ0uKWekiZ5g8wtr28cw==",
+      "dev": true,
       "license": "MIT",
       "dependencies": {
         "end-of-stream": "^1.1.0",
@@ -12505,18 +12014,6 @@
       ],
       "license": "MIT"
     },
-    "node_modules/quick-lru": {
-      "version": "5.1.1",
-      "resolved": "https://registry.npmjs.org/quick-lru/-/quick-lru-5.1.1.tgz",
-      "integrity": "sha512-WuyALRjWPDGtt/wzJiadO5AXY+8hZ80hVpe6MyivgraREW751X3SbhRvG3eLKOYN+8VEvqLcf3wdnt44Z4S4SA==",
-      "license": "MIT",
-      "engines": {
-        "node": ">=10"
-      },
-      "funding": {
-        "url": "https://github.com/sponsors/sindresorhus"
-      }
-    },
     "node_modules/randombytes": {
       "version": "2.1.0",
       "resolved": "https://registry.npmjs.org/randombytes/-/randombytes-2.1.0.tgz",
@@ -12917,12 +12414,6 @@
         "url": "https://github.com/sponsors/ljharb"
       }
     },
-    "node_modules/resolve-alpn": {
-      "version": "1.2.1",
-      "resolved": "https://registry.npmjs.org/resolve-alpn/-/resolve-alpn-1.2.1.tgz",
-      "integrity": "sha512-0a1F4l73/ZFZOakJnQ3FvkJ2+gSTQWz/r2KE5OdDY0TxPm5h4GkqkWWfM47T7HsbnOtcJVEF4epCVy6u7Q3K+g==",
-      "license": "MIT"
-    },
     "node_modules/resolve-from": {
       "version": "5.0.0",
       "resolved": "https://registry.npmjs.org/resolve-from/-/resolve-from-5.0.0.tgz",
@@ -12933,18 +12424,6 @@
         "node": ">=8"
       }
     },
-    "node_modules/responselike": {
-      "version": "2.0.1",
-      "resolved": "https://registry.npmjs.org/responselike/-/responselike-2.0.1.tgz",
-      "integrity": "sha512-4gl03wn3hj1HP3yzgdI7d3lCkF95F21Pz4BPGvKHinyQzALR5CapwC8yIi0Rh58DEMQ/SguC03wFj2k0M/mHhw==",
-      "license": "MIT",
-      "dependencies": {
-        "lowercase-keys": "^2.0.0"
-      },
-      "funding": {
-        "url": "https://github.com/sponsors/sindresorhus"
-      }
-    },
     "node_modules/restore-cursor": {
       "version": "2.0.0",
       "resolved": "https://registry.npmjs.org/restore-cursor/-/restore-cursor-2.0.0.tgz",
@@ -14348,15 +13827,6 @@
         "node": ">=4"
       }
     },
-    "node_modules/to-readable-stream": {
-      "version": "1.0.0",
-      "resolved": "https://registry.npmjs.org/to-readable-stream/-/to-readable-stream-1.0.0.tgz",
-      "integrity": "sha512-Iq25XBt6zD5npPhlLVXGFN3/gyR2/qODcKNNyTMd4vbm39HUaOiAM4PMq0eMVC/Tkxz+Zjdsc55g9yyz+Yq00Q==",
-      "license": "MIT",
-      "engines": {
-        "node": ">=6"
-      }
-    },
     "node_modules/to-regex-range": {
       "version": "5.0.1",
       "resolved": "https://registry.npmjs.org/to-regex-range/-/to-regex-range-5.0.1.tgz",
@@ -14728,18 +14198,6 @@
         "punycode": "^2.1.0"
       }
     },
-    "node_modules/url-parse-lax": {
-      "version": "3.0.0",
-      "resolved": "https://registry.npmjs.org/url-parse-lax/-/url-parse-lax-3.0.0.tgz",
-      "integrity": "sha512-NjFKA0DidqPa5ciFcSrXnAltTtzz84ogy+NebPvfEgAck0+TNg4UJ4IN+fB7zRZfbgUf0syOo9MDxFkDSMuFaQ==",
-      "license": "MIT",
-      "dependencies": {
-        "prepend-http": "^2.0.0"
-      },
-      "engines": {
-        "node": ">=4"
-      }
-    },
     "node_modules/util-deprecate": {
       "version": "1.0.2",
       "resolved": "https://registry.npmjs.org/util-deprecate/-/util-deprecate-1.0.2.tgz",
diff --git a/package.json b/package.json
index 7f54e8f3f..eb577ce3e 100644
--- a/package.json
+++ b/package.json
@@ -131,7 +131,6 @@
     "is-class": "^0.0.9",
     "is-docker": "^2.2.1",
     "is-interactive": "^1",
-    "is-online": "^9",
     "is-root": "^2",
     "js-yaml": "^4.1.0",
     "jsonfile": "^2.4.0",
diff --git a/sources/github.js b/sources/github.js
index 6bd217957..7195d41ff 100644
--- a/sources/github.js
+++ b/sources/github.js
@@ -6,8 +6,6 @@ const fs = require('fs');
 const os = require('os');
 const path = require('path');
 
-const {Octokit} = require('@octokit/rest');
-
 // Github
 const githubTokenCache = 'github.tokens';
 const gitHubLandoKey = 'github.lando.id_rsa';
@@ -31,7 +29,7 @@ const parseTokens = tokens => _.flatten([getTokens(tokens), [{name: 'add or refr
 
 // Helper to post a github ssh key
 const postKey = (keyDir, token, id) => {
-  const octokit = new Octokit({auth: token});
+  const octokit = require('../utils/get-octokit')({auth: token});
   return octokit.users.createPublicSshKeyForAuthenticatedUser({
     title: id,
     key: _.trim(fs.readFileSync(path.join(keyDir, `${gitHubLandoKey}.pub`), 'utf8')),
@@ -52,7 +50,7 @@ const postKey = (keyDir, token, id) => {
 
 // Helper to set caches
 const setCaches = (options, lando) => {
-  const octokit = new Octokit({auth: options['github-auth']});
+  const octokit = require('../utils/get-octokit')({auth: options['github-auth']});
   return octokit.rest.users.getAuthenticated()
   .then(user => {
     const metaData = lando.cache.get(`${options.name}.meta.cache`) || {};
@@ -74,7 +72,7 @@ const showTokenEntry = (source, answer, tkez = []) => ((_.isEmpty(tkez) || answe
 const getRepos = answers => {
   // Log
   console.log('Getting your GitHub repos... this may take a moment if you have a lot');
-  const octokit = new Octokit({auth: answers['github-auth']});
+  const octokit = require('../utils/get-octokit')({auth: answers['github-auth']});
   return octokit.paginate('GET /user/repos', {affliation: 'owner,collaborator,organization_member', per_page: 100})
   .then(results => results.map(result => ({name: result.full_name, value: result.ssh_url})))
   .catch(gerror => {
diff --git a/utils/get-octokit.js b/utils/get-octokit.js
new file mode 100644
index 000000000..35e01f739
--- /dev/null
+++ b/utils/get-octokit.js
@@ -0,0 +1,14 @@
+'use strict';
+
+const {Octokit} = require('@octokit/rest');
+
+const {HttpsAgent} = require('@npmcli/agent');
+
+const defaults = {
+  userAgent: 'Lando/unknown',
+  request: {
+    agent: new HttpsAgent({family: 4}),
+  },
+};
+
+module.exports = (options = {}) => new Octokit({...defaults, ...options});
diff --git a/utils/get-plugin-add-task.js b/utils/get-plugin-add-task.js
index c26990a84..ce3ca3624 100644
--- a/utils/get-plugin-add-task.js
+++ b/utils/get-plugin-add-task.js
@@ -26,11 +26,8 @@ module.exports = (plugin, {
       }
     },
     canInstall: async () => {
-      const online = await require('is-online')();
-      // throw error if not online
-      if (!online) throw new Error('Cannot detect connection to internet!');
-      // attempt ti get info on the plugin
       await Plugin.info(plugin);
+      return true;
     },
     task: async (ctx, task) => {
       try {
diff --git a/utils/get-plugin-update-task.js b/utils/get-plugin-update-task.js
index 1173290cb..78df89603 100644
--- a/utils/get-plugin-update-task.js
+++ b/utils/get-plugin-update-task.js
@@ -14,10 +14,7 @@ module.exports = (plugin, {
     title: `Updating ${pkg.name} to v${pkg.peg}`,
     description: pkg.name,
     canInstall: async () => {
-      const online = await require('is-online')();
-      // throw error if not online
-      if (!online) throw new Error('Cannot detect connection to internet!');
-      // or true
+      await Plugin.info(plugin);
       return true;
     },
     task: async (ctx, task) => {