diff --git a/.changeset/spotty-buckets-reflect.md b/.changeset/spotty-buckets-reflect.md
new file mode 100644
index 00000000..674623db
--- /dev/null
+++ b/.changeset/spotty-buckets-reflect.md
@@ -0,0 +1,5 @@
+---
+"@webstone/cli": minor
+---
+
+Add a `webstone web configure deployment` CLI command.
diff --git a/.gitpod.yml b/.gitpod.yml
index 8170a823..e1b2d57b 100644
--- a/.gitpod.yml
+++ b/.gitpod.yml
@@ -17,10 +17,10 @@ tasks:
     command: |
       cd webstone-dev-app
       while [ ! -f ../webstone/packages/cli/dist/bin.js ]; do sleep 1; done
-      pnpm link ../webstone/packages/cli
+      pnpm add -w -D ../webstone/packages/cli
       export HMR_HOST=`gp url 3000`
       pnpm ws dev gitpod web-patch-svelte-config-js
-      pnpm dev
+      pnpm ws dev
     openMode: split-right
 
 ports:
diff --git a/packages/cli/bin b/packages/cli/bin
index e3a73877..1e39c3fd 100755
--- a/packages/cli/bin
+++ b/packages/cli/bin
@@ -1,7 +1,7 @@
 #!/usr/bin/env node
 if (process.argv.includes("--tests")) {
   require('ts-node').register({ project: `${__dirname}/tsconfig.json` })
-  require(`${__dirname}/src/bin`).run(process.argv)
+  require(`${__dirname}/src/bin`).run()
 } else {
-  require(`${__dirname}/dist/bin`).run(process.argv);
+  require(`${__dirname}/dist/bin`).run();
 }
diff --git a/packages/cli/package.json b/packages/cli/package.json
index e82f154f..242f72c7 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -12,7 +12,7 @@
     "clean": "rm -rf ./dist",
     "compile": "tsc -p .",
     "copy-templates": "if [ -e ./src/templates ]; then cp -a ./src/templates ./dist/; fi",
-    "dev": "pnpm copy-templates && pnpm dev:watch-src & pnpm dev:watch-templates",
+    "dev": "pnpm clean && pnpm copy-templates && pnpm dev:watch-src & pnpm dev:watch-templates",
     "dev:watch-src": "tsc -w",
     "dev:watch-templates": "npm-watch copy-templates",
     "format": "prettier --write **/*.{js,ts,tsx,json}",
diff --git a/packages/cli/src/bin.ts b/packages/cli/src/bin.ts
index 82a075ba..35edfe10 100644
--- a/packages/cli/src/bin.ts
+++ b/packages/cli/src/bin.ts
@@ -1,6 +1,6 @@
 const { build } = require("gluegun");
 
-async function run(argv) {
+async function run() {
   const cli = build()
     .brand("webstone")
     .src(__dirname)
@@ -21,7 +21,7 @@ async function run(argv) {
       // "template",
     ])
     .create();
-  const toolbox = await cli.run(argv);
+  const toolbox = await cli.run(process.argv);
 
   // Return to use it in tests
   return toolbox;
diff --git a/packages/cli/src/commands/web/configure/deployment.ts b/packages/cli/src/commands/web/configure/deployment.ts
new file mode 100644
index 00000000..de7ea927
--- /dev/null
+++ b/packages/cli/src/commands/web/configure/deployment.ts
@@ -0,0 +1,80 @@
+import type { GluegunCommand, GluegunToolbox } from "gluegun";
+import type { WebToolbox } from "../../../extensions/web/types";
+
+interface WebstoneToolbox extends GluegunToolbox, WebToolbox {}
+
+const command: GluegunCommand = {
+  // @ts-ignore: WebstoneToolbox extends GluegunToolbox, ignore TS error.
+  run: async (toolbox: WebstoneToolbox) => {
+    const { print, prompt, web } = toolbox;
+
+    const availableAdapters = web.configure.deployment.availableAdapters;
+    const adapterPromptResult = await prompt.ask({
+      type: "select",
+      name: "adapter",
+      message: `Where would you like to deploy the "web" service to?`,
+      choices: availableAdapters.map(
+        (adapter) => `${adapter.name} (${adapter.npmPackage})`
+      ),
+    });
+    let adapterIdentifier = "";
+    if (adapterPromptResult && adapterPromptResult.adapter)
+      adapterIdentifier = adapterPromptResult.adapter;
+
+    if (adapterIdentifier === "") {
+      print.error("Please choose an adapter.");
+      return;
+    }
+
+    const chosenAdapter = availableAdapters.find((availableAdapter) =>
+      adapterIdentifier.includes(availableAdapter.npmPackage)
+    );
+    if (!chosenAdapter) {
+      print.error(`The chosen adapter ${adapterIdentifier} is not available.`);
+      return;
+    }
+
+    const nextStepsInstructions: string[] = [];
+    if (web.configure.deployment.isAnyAdapterInstalled()) {
+      const installedAdapterNpmPackage = web.configure.deployment.getInstalledAdapterPackageName();
+      const installedAdapter = availableAdapters.find(
+        (adapter) => adapter.npmPackage === installedAdapterNpmPackage
+      );
+
+      if (installedAdapterNpmPackage === chosenAdapter.npmPackage) {
+        print.info(`Adapter ${chosenAdapter.name} is already installed.`);
+        return;
+      }
+
+      if (!installedAdapter) {
+        print.error(
+          `Adapter ${installedAdapterNpmPackage} should be installed, but isn't... This is an unexpected error, please manually review the "services/web/package.json file."`
+        );
+        return;
+      }
+      const isReplaceInstalledAdapter = await prompt.confirm(
+        `The ${installedAdapter.name} adapter is already installed. Would you like to replace it with ${chosenAdapter.name}?`
+      );
+      if (isReplaceInstalledAdapter) {
+        await web.configure.deployment.removeAdapter(installedAdapter);
+        nextStepsInstructions.push(
+          `- to completely remove the ${installedAdapter.name} adapter: ${installedAdapter.nextStepsDocsLink}`
+        );
+      } else {
+        return;
+      }
+    }
+
+    await web.configure.deployment.installAdapter(chosenAdapter);
+    nextStepsInstructions.push(
+      `- to finalize the configuration of the newly installed ${chosenAdapter.name} adapter, undo the changes at: ${chosenAdapter.nextStepsDocsLink}`
+    );
+    print.highlight(
+      `\nPlease perform the following next steps by reading the docs:\n${nextStepsInstructions.join(
+        "\n"
+      )}`
+    );
+  },
+};
+
+module.exports = command;
diff --git a/packages/cli/src/extensions/pnpm.ts b/packages/cli/src/extensions/pnpm.ts
new file mode 100644
index 00000000..f630e51f
--- /dev/null
+++ b/packages/cli/src/extensions/pnpm.ts
@@ -0,0 +1,11 @@
+import type { GluegunToolbox } from "gluegun";
+
+import add from "../toolbox/pnpm/add";
+import remove from "../toolbox/pnpm/remove";
+
+export default (toolbox: GluegunToolbox) => {
+  toolbox.pnpm = {
+    add,
+    remove,
+  };
+};
diff --git a/packages/cli/src/extensions/web.ts b/packages/cli/src/extensions/web.ts
new file mode 100644
index 00000000..26cf7ac2
--- /dev/null
+++ b/packages/cli/src/extensions/web.ts
@@ -0,0 +1,17 @@
+import type { GluegunToolbox } from "gluegun";
+import type { WebToolbox } from "./web/types";
+
+import webConfigureDeployment from "./web/configure/deployment";
+
+export default (toolbox: GluegunToolbox) => {
+  const webToolbox: WebToolbox = {
+    web: {
+      configure: {
+        deployment: webConfigureDeployment,
+      },
+    },
+  };
+  toolbox.web = {
+    ...webToolbox.web,
+  };
+};
diff --git a/packages/cli/src/extensions/web/configure/deployment.ts b/packages/cli/src/extensions/web/configure/deployment.ts
new file mode 100644
index 00000000..c824e090
--- /dev/null
+++ b/packages/cli/src/extensions/web/configure/deployment.ts
@@ -0,0 +1,13 @@
+import { availableAdapters } from "../../../toolbox/web/configure/deployment/adapters";
+import getInstalledAdapterPackageName from "../../../toolbox/web/configure/deployment/get-installed-adapter-package-name";
+import installAdapter from "../../../toolbox/web/configure/deployment/install-adapter";
+import isAnyAdapterInstalled from "../../../toolbox/web/configure/deployment/is-any-adapter-installed";
+import removeAdapter from "../../../toolbox/web/configure/deployment/remove-adapter";
+
+export default {
+  availableAdapters,
+  getInstalledAdapterPackageName,
+  installAdapter,
+  isAnyAdapterInstalled,
+  removeAdapter,
+};
diff --git a/packages/cli/src/extensions/web/types.d.ts b/packages/cli/src/extensions/web/types.d.ts
new file mode 100644
index 00000000..9d5f708a
--- /dev/null
+++ b/packages/cli/src/extensions/web/types.d.ts
@@ -0,0 +1,15 @@
+import type { Adapter } from "../../toolbox/web/configure/deployment/types";
+
+export interface WebToolbox {
+  web: {
+    configure: {
+      deployment: {
+        availableAdapters: Adapter[];
+        getInstalledAdapterPackageName: () => string;
+        installAdapter: (adapter: Adapter) => Promise<void>;
+        isAnyAdapterInstalled: () => boolean;
+        removeAdapter: (adapter: Adapter) => Promise<void>;
+      };
+    };
+  };
+}
diff --git a/packages/cli/src/toolbox/pnpm/add.ts b/packages/cli/src/toolbox/pnpm/add.ts
new file mode 100644
index 00000000..dc911ea6
--- /dev/null
+++ b/packages/cli/src/toolbox/pnpm/add.ts
@@ -0,0 +1,11 @@
+import type { PnpmOptions } from "./types";
+
+import { system } from "gluegun";
+
+export default async (packageName: string, options?: PnpmOptions) => {
+  const dev = options?.dev ? "-D " : "";
+  const stdout = await system.run(`pnpm add ${dev}${packageName}`, {
+    cwd: options?.dir || ".",
+  });
+  return { success: true, stdout };
+};
diff --git a/packages/cli/src/toolbox/pnpm/remove.ts b/packages/cli/src/toolbox/pnpm/remove.ts
new file mode 100644
index 00000000..19ef9f76
--- /dev/null
+++ b/packages/cli/src/toolbox/pnpm/remove.ts
@@ -0,0 +1,11 @@
+import type { PnpmOptions } from "./types";
+
+import { system } from "gluegun";
+
+export default async (packageName: string, options?: PnpmOptions) => {
+  const dev = options?.dev ? "-D " : "";
+  const stdout = await system.run(`pnpm remove ${dev}${packageName}`, {
+    cwd: options?.dir || "",
+  });
+  return { success: true, stdout };
+};
diff --git a/packages/cli/src/toolbox/pnpm/types.d.ts b/packages/cli/src/toolbox/pnpm/types.d.ts
new file mode 100644
index 00000000..9dba9dcc
--- /dev/null
+++ b/packages/cli/src/toolbox/pnpm/types.d.ts
@@ -0,0 +1,4 @@
+export type PnpmOptions = {
+  dev: boolean;
+  dir: string;
+};
diff --git a/packages/cli/src/toolbox/web/configure/deployment/adapters.ts b/packages/cli/src/toolbox/web/configure/deployment/adapters.ts
new file mode 100644
index 00000000..fdce4258
--- /dev/null
+++ b/packages/cli/src/toolbox/web/configure/deployment/adapters.ts
@@ -0,0 +1,50 @@
+import { Adapter } from "./types";
+
+export const availableAdapters: Adapter[] = [
+  {
+    // Enable & test when https://github.com/architect/architect/issues/1236 is resolved.
+    //   identifier: "adapter-begin",
+    //   name: "Begin / Architect",
+    //   npmPackage: "@architect/sveltekit-adapter",
+    //   nextStepsDocsLink: "https://github.com/architect/sveltekit-adapter"
+    // }, {
+    identifier: "adapter-cloudflare-workers",
+    name: "Cloudflare Workers",
+    npmPackage: "@sveltejs/adapter-cloudflare-workers",
+    npmPackageVersion: "@next",
+    nextStepsDocsLink:
+      "https://github.com/sveltejs/kit/tree/master/packages/adapter-cloudflare-workers",
+  },
+  {
+    identifier: "adapter-netlify",
+    name: "Netlify",
+    npmPackage: "@sveltejs/adapter-netlify",
+    npmPackageVersion: "@next",
+    nextStepsDocsLink:
+      "https://github.com/sveltejs/kit/tree/master/packages/adapter-netlify",
+  },
+  {
+    identifier: "adapter-node",
+    name: "Node.js",
+    npmPackage: "@sveltejs/adapter-node",
+    npmPackageVersion: "@next",
+    nextStepsDocsLink:
+      "https://github.com/sveltejs/kit/tree/master/packages/adapter-node",
+  },
+  {
+    identifier: "adapter-static",
+    name: "Static",
+    npmPackage: "@sveltejs/adapter-static",
+    npmPackageVersion: "@next",
+    nextStepsDocsLink:
+      "https://github.com/sveltejs/kit/tree/master/packages/adapter-static",
+  },
+  {
+    identifier: "adapter-vercel",
+    name: "Vercel",
+    npmPackage: "@sveltejs/adapter-vercel",
+    npmPackageVersion: "@next",
+    nextStepsDocsLink:
+      "https://github.com/sveltejs/kit/tree/master/packages/adapter-vercel",
+  },
+];
diff --git a/packages/cli/src/toolbox/web/configure/deployment/get-installed-adapter-package-name.ts b/packages/cli/src/toolbox/web/configure/deployment/get-installed-adapter-package-name.ts
new file mode 100644
index 00000000..206390e3
--- /dev/null
+++ b/packages/cli/src/toolbox/web/configure/deployment/get-installed-adapter-package-name.ts
@@ -0,0 +1,14 @@
+import { filesystem } from "gluegun";
+import { availableAdapters } from "./adapters";
+
+export default () => {
+  const webPackageJson = filesystem.read("./services/web/package.json", "json");
+  const availableAdapterNpmPackages = availableAdapters.map(
+    (adapter) => adapter.npmPackage
+  );
+  return (
+    Object.keys(webPackageJson.devDependencies).find((devDependency) =>
+      availableAdapterNpmPackages.includes(devDependency)
+    ) || ""
+  );
+};
diff --git a/packages/cli/src/toolbox/web/configure/deployment/install-adapter.ts b/packages/cli/src/toolbox/web/configure/deployment/install-adapter.ts
new file mode 100644
index 00000000..3368b839
--- /dev/null
+++ b/packages/cli/src/toolbox/web/configure/deployment/install-adapter.ts
@@ -0,0 +1,17 @@
+import type { Adapter } from "./types";
+
+import { print } from "gluegun";
+import add from "../../../pnpm/add";
+
+export default async (adapter: Adapter) => {
+  const spinner = print.spin(
+    `Adding adapter package "${adapter.npmPackage}${
+      adapter.npmPackageVersion || ""
+    }"...`
+  );
+  await add(`${adapter.npmPackage}${adapter.npmPackageVersion || ""}`, {
+    dev: true,
+    dir: "./services/web",
+  });
+  spinner.succeed(`Adapter added: ${adapter.npmPackage}`);
+};
diff --git a/packages/cli/src/toolbox/web/configure/deployment/is-any-adapter-installed.ts b/packages/cli/src/toolbox/web/configure/deployment/is-any-adapter-installed.ts
new file mode 100644
index 00000000..6fbb0851
--- /dev/null
+++ b/packages/cli/src/toolbox/web/configure/deployment/is-any-adapter-installed.ts
@@ -0,0 +1,3 @@
+import getInstalledAdapterPackageName from "./get-installed-adapter-package-name";
+
+export default () => !!getInstalledAdapterPackageName();
diff --git a/packages/cli/src/toolbox/web/configure/deployment/remove-adapter.ts b/packages/cli/src/toolbox/web/configure/deployment/remove-adapter.ts
new file mode 100644
index 00000000..729cf570
--- /dev/null
+++ b/packages/cli/src/toolbox/web/configure/deployment/remove-adapter.ts
@@ -0,0 +1,15 @@
+import type { Adapter } from "./types";
+
+import { print } from "gluegun";
+import remove from "../../../pnpm/remove";
+
+export default async (adapter: Adapter) => {
+  const spinner = print.spin(
+    `Removing adapter package "${adapter.npmPackage}"...`
+  );
+  await remove(adapter.npmPackage, {
+    dev: true,
+    dir: "./services/web",
+  });
+  spinner.succeed(`Adapter removed: ${adapter.npmPackage}`);
+};
diff --git a/packages/cli/src/toolbox/web/configure/deployment/types.d.ts b/packages/cli/src/toolbox/web/configure/deployment/types.d.ts
new file mode 100644
index 00000000..d2c1b187
--- /dev/null
+++ b/packages/cli/src/toolbox/web/configure/deployment/types.d.ts
@@ -0,0 +1,13 @@
+export type Adapter = {
+  identifier:
+    | "adapter-begin"
+    | "adapter-cloudflare-workers"
+    | "adapter-netlify"
+    | "adapter-node"
+    | "adapter-static"
+    | "adapter-vercel";
+  name: string;
+  npmPackage: string;
+  npmPackageVersion?: string;
+  nextStepsDocsLink: string;
+};
diff --git a/packages/cli/src/types.ts b/packages/cli/src/types.ts
deleted file mode 100644
index 07a21bbf..00000000
--- a/packages/cli/src/types.ts
+++ /dev/null
@@ -1 +0,0 @@
-// export types
diff --git a/packages/cli/tsconfig.json b/packages/cli/tsconfig.json
index b6a20dc2..26719b0d 100644
--- a/packages/cli/tsconfig.json
+++ b/packages/cli/tsconfig.json
@@ -12,13 +12,13 @@
     ],
     "module": "commonjs",
     "moduleResolution": "node",
-    "noImplicitAny": false,
+    "noImplicitAny": true,
     "noImplicitThis": true,
     "noUnusedLocals": true,
     "sourceMap": false,
     "inlineSourceMap": true,
     "outDir": "dist",
-    "strict": false,
+    "strict": true,
     "target": "es5",
     "declaration": true,
     "declarationDir": "dist/types"