diff --git a/.changeset/quiet-pots-kiss.md b/.changeset/quiet-pots-kiss.md
new file mode 100644
index 000000000000..4cef5243a2dc
--- /dev/null
+++ b/.changeset/quiet-pots-kiss.md
@@ -0,0 +1,7 @@
+---
+"wrangler": patch
+---
+
+feat: reload server on configuration changes, the values passed into the server during restart will be `bindings`
+
+resolves #439
diff --git a/packages/wrangler/src/index.tsx b/packages/wrangler/src/index.tsx
index 0e9b9141f5e2..ed1730eaef4f 100644
--- a/packages/wrangler/src/index.tsx
+++ b/packages/wrangler/src/index.tsx
@@ -4,6 +4,7 @@ import path from "node:path";
 import { setTimeout } from "node:timers/promises";
 import TOML from "@iarna/toml";
 import chalk from "chalk";
+import { watch } from "chokidar";
 import { execa } from "execa";
 import { findUp } from "find-up";
 import getPort from "get-port";
@@ -1035,197 +1036,229 @@ function createCLIParser(argv: string[]) {
         });
     },
     async (args) => {
-      await printWranglerBanner();
-      const configPath =
-        (args.config as ConfigPath) ||
-        (args.script && findWranglerToml(path.dirname(args.script)));
-      const config = readConfig(configPath, args);
-      const entry = await getEntry(args, config, "dev");
-
-      if (config.services && config.services.length > 0) {
-        logger.warn(
-          `This worker is bound to live services: ${config.services
-            .map(
-              (service) =>
-                `${service.binding} (${service.service}${
-                  service.environment ? `@${service.environment}` : ""
-                })`
-            )
-            .join(", ")}`
-        );
-      }
-
-      if (args.inspect) {
-        logger.warn(
-          "Passing --inspect is unnecessary, now you can always connect to devtools."
-        );
-      }
-
-      if (args["experimental-public"]) {
-        logger.warn(
-          "The --experimental-public field is experimental and will change in the future."
-        );
-      }
+      let watcher: ReturnType<typeof watch> | undefined;
+      try {
+        await printWranglerBanner();
+        const configPath =
+          (args.config as ConfigPath) ||
+          ((args.script &&
+            findWranglerToml(path.dirname(args.script))) as ConfigPath);
+        let config = readConfig(configPath, args);
+
+        if (config.configPath) {
+          watcher = watch(config.configPath, {
+            persistent: true,
+          }).on("change", async (_event) => {
+            // TODO: Do we need to handle different `_event` types differently?
+            //       e.g. what if the file is deleted, or added?
+            config = readConfig(configPath, args);
+            if (config.configPath) {
+              logger.log(`${path.basename(config.configPath)} changed...`);
+              rerender(await getDevReactElement(config));
+            }
+          });
+        }
 
-      if (args.public) {
-        throw new Error(
-          "The --public field has been renamed to --experimental-public, and will change behaviour in the future."
-        );
-      }
+        const entry = await getEntry(args, config, "dev");
 
-      const upstreamProtocol =
-        args["upstream-protocol"] || config.dev.upstream_protocol;
-      if (upstreamProtocol === "http") {
-        logger.warn(
-          "Setting upstream-protocol to http is not currently implemented.\n" +
-            "If this is required in your project, please add your use case to the following issue:\n" +
-            "https://github.com/cloudflare/wrangler2/issues/583."
-        );
-      }
+        if (config.services && config.services.length > 0) {
+          logger.warn(
+            `This worker is bound to live services: ${config.services
+              .map(
+                (service) =>
+                  `${service.binding} (${service.service}${
+                    service.environment ? `@${service.environment}` : ""
+                  })`
+              )
+              .join(", ")}`
+          );
+        }
 
-      // TODO: if worker_dev = false and no routes, then error (only for dev)
+        if (args.inspect) {
+          logger.warn(
+            "Passing --inspect is unnecessary, now you can always connect to devtools."
+          );
+        }
 
-      // Compute zone info from the `host` and `route` args and config;
-      let host = args.host || config.dev.host;
-      let zoneId: string | undefined;
+        if (args["experimental-public"]) {
+          logger.warn(
+            "The --experimental-public field is experimental and will change in the future."
+          );
+        }
 
-      if (!args.local) {
-        if (host) {
-          zoneId = await getZoneIdFromHost(host);
+        if (args.public) {
+          throw new Error(
+            "The --public field has been renamed to --experimental-public, and will change behaviour in the future."
+          );
         }
-        const routes = args.routes || config.route || config.routes;
-        if (!zoneId && routes) {
-          const firstRoute = Array.isArray(routes) ? routes[0] : routes;
-          const zone = await getZoneForRoute(firstRoute);
-          if (zone) {
-            zoneId = zone.id;
-            host = zone.host;
-          }
+
+        const upstreamProtocol =
+          args["upstream-protocol"] || config.dev.upstream_protocol;
+        if (upstreamProtocol === "http") {
+          logger.warn(
+            "Setting upstream-protocol to http is not currently implemented.\n" +
+              "If this is required in your project, please add your use case to the following issue:\n" +
+              "https://github.com/cloudflare/wrangler2/issues/583."
+          );
         }
-      }
 
-      const nodeCompat = args.nodeCompat ?? config.node_compat;
-      if (nodeCompat) {
-        logger.warn(
-          "Enabling node.js compatibility mode for built-ins and globals. This is experimental and has serious tradeoffs. Please see https://github.com/ionic-team/rollup-plugin-node-polyfills/ for more details."
-        );
-      }
+        // TODO: if worker_dev = false and no routes, then error (only for dev)
 
-      const bindings = {
-        kv_namespaces: config.kv_namespaces?.map(
-          ({ binding, preview_id, id: _id }) => {
-            // In `dev`, we make folks use a separate kv namespace called
-            // `preview_id` instead of `id` so that they don't
-            // break production data. So here we check that a `preview_id`
-            // has actually been configured.
-            // This whole block of code will be obsoleted in the future
-            // when we have copy-on-write for previews on edge workers.
-            if (!preview_id) {
-              // TODO: This error has to be a _lot_ better, ideally just asking
-              // to create a preview namespace for the user automatically
-              throw new Error(
-                `In development, you should use a separate kv namespace than the one you'd use in production. Please create a new kv namespace with "wrangler kv:namespace create <name> --preview" and add its id as preview_id to the kv_namespace "${binding}" in your wrangler.toml`
-              ); // Ugh, I really don't like this message very much
-            }
-            return {
-              binding,
-              id: preview_id,
-            };
+        // Compute zone info from the `host` and `route` args and config;
+        let host = args.host || config.dev.host;
+        let zoneId: string | undefined;
+
+        if (!args.local) {
+          if (host) {
+            zoneId = await getZoneIdFromHost(host);
           }
-        ),
-        // Use a copy of combinedVars since we're modifying it later
-        vars: getVarsForDev(config),
-        wasm_modules: config.wasm_modules,
-        text_blobs: config.text_blobs,
-        data_blobs: config.data_blobs,
-        durable_objects: config.durable_objects,
-        r2_buckets: config.r2_buckets?.map(
-          ({ binding, preview_bucket_name, bucket_name: _bucket_name }) => {
-            // same idea as kv namespace preview id,
-            // same copy-on-write TODO
-            if (!preview_bucket_name) {
-              throw new Error(
-                `In development, you should use a separate r2 bucket than the one you'd use in production. Please create a new r2 bucket with "wrangler r2 bucket create <name>" and add its name as preview_bucket_name to the r2_buckets "${binding}" in your wrangler.toml`
-              );
+          const routes = args.routes || config.route || config.routes;
+          if (!zoneId && routes) {
+            const firstRoute = Array.isArray(routes) ? routes[0] : routes;
+            const zone = await getZoneForRoute(firstRoute);
+            if (zone) {
+              zoneId = zone.id;
+              host = zone.host;
             }
-            return {
-              binding,
-              bucket_name: preview_bucket_name,
-            };
           }
-        ),
-        services: config.services,
-        unsafe: config.unsafe?.bindings,
-      };
+        }
 
-      // mask anything that was overridden in .dev.vars
-      // so that we don't log potential secrets into the terminal
-      const maskedVars = { ...bindings.vars };
-      for (const key of Object.keys(maskedVars)) {
-        if (maskedVars[key] !== config.vars[key]) {
-          // This means it was overridden in .dev.vars
-          // so let's mask it
-          maskedVars[key] = "(hidden)";
+        const nodeCompat = args.nodeCompat ?? config.node_compat;
+        if (nodeCompat) {
+          logger.warn(
+            "Enabling node.js compatibility mode for built-ins and globals. This is experimental and has serious tradeoffs. Please see https://github.com/ionic-team/rollup-plugin-node-polyfills/ for more details."
+          );
         }
-      }
 
-      // now log all available bindings into the terminal
-      printBindings({
-        ...bindings,
-        vars: maskedVars,
-      });
+        // eslint-disable-next-line no-inner-declarations
+        async function getBindings(configParam: Config) {
+          return {
+            kv_namespaces: configParam.kv_namespaces?.map(
+              ({ binding, preview_id, id: _id }) => {
+                // In `dev`, we make folks use a separate kv namespace called
+                // `preview_id` instead of `id` so that they don't
+                // break production data. So here we check that a `preview_id`
+                // has actually been configured.
+                // This whole block of code will be obsoleted in the future
+                // when we have copy-on-write for previews on edge workers.
+                if (!preview_id) {
+                  // TODO: This error has to be a _lot_ better, ideally just asking
+                  // to create a preview namespace for the user automatically
+                  throw new Error(
+                    `In development, you should use a separate kv namespace than the one you'd use in production. Please create a new kv namespace with "wrangler kv:namespace create <name> --preview" and add its id as preview_id to the kv_namespace "${binding}" in your wrangler.toml`
+                  ); // Ugh, I really don't like this message very much
+                }
+                return {
+                  binding,
+                  id: preview_id,
+                };
+              }
+            ),
+            // Use a copy of combinedVars since we're modifying it later
+            vars: getVarsForDev(configParam),
+            wasm_modules: configParam.wasm_modules,
+            text_blobs: configParam.text_blobs,
+            data_blobs: configParam.data_blobs,
+            durable_objects: configParam.durable_objects,
+            r2_buckets: configParam.r2_buckets?.map(
+              ({ binding, preview_bucket_name, bucket_name: _bucket_name }) => {
+                // same idea as kv namespace preview id,
+                // same copy-on-write TODO
+                if (!preview_bucket_name) {
+                  throw new Error(
+                    `In development, you should use a separate r2 bucket than the one you'd use in production. Please create a new r2 bucket with "wrangler r2 bucket create <name>" and add its name as preview_bucket_name to the r2_buckets "${binding}" in your wrangler.toml`
+                  );
+                }
+                return {
+                  binding,
+                  bucket_name: preview_bucket_name,
+                };
+              }
+            ),
+            services: configParam.services,
+            unsafe: configParam.unsafe?.bindings,
+          };
+        }
 
-      const { waitUntilExit } = render(
-        <Dev
-          name={getScriptName(args, config)}
-          entry={entry}
-          env={args.env}
-          zone={zoneId}
-          host={host}
-          rules={getRules(config)}
-          legacyEnv={isLegacyEnv(config)}
-          minify={args.minify ?? config.minify}
-          nodeCompat={nodeCompat}
-          build={config.build || {}}
-          initialMode={args.local ? "local" : "remote"}
-          jsxFactory={args["jsx-factory"] || config.jsx_factory}
-          jsxFragment={args["jsx-fragment"] || config.jsx_fragment}
-          tsconfig={args.tsconfig ?? config.tsconfig}
-          upstreamProtocol={upstreamProtocol}
-          localProtocol={args["local-protocol"] || config.dev.local_protocol}
-          enableLocalPersistence={
-            args["experimental-enable-local-persistence"] || false
-          }
-          accountId={config.account_id}
-          assetPaths={getAssetPaths(
-            config,
-            args.site,
-            args.siteInclude,
-            args.siteExclude
-          )}
-          port={
-            args.port ||
-            config.dev.port ||
-            (await getPort({ port: DEFAULT_LOCAL_PORT }))
-          }
-          ip={args.ip || config.dev.ip}
-          inspectorPort={
-            args["inspector-port"] ?? (await getPort({ port: 9229 }))
-          }
-          public={args["experimental-public"]}
-          compatibilityDate={getDevCompatibilityDate(
-            config,
-            args["compatibility-date"]
-          )}
-          compatibilityFlags={
-            args["compatibility-flags"] || config.compatibility_flags
+        const getLocalPort = memoizeGetPort(DEFAULT_LOCAL_PORT);
+        const getInspectorPort = memoizeGetPort(9229);
+
+        // eslint-disable-next-line no-inner-declarations
+        async function getDevReactElement(configParam: Config) {
+          // now log all available bindings into the terminal
+          const bindings = await getBindings(configParam);
+          // mask anything that was overridden in .dev.vars
+          // so that we don't log potential secrets into the terminal
+          const maskedVars = { ...bindings.vars };
+          for (const key of Object.keys(maskedVars)) {
+            if (maskedVars[key] !== configParam.vars[key]) {
+              // This means it was overridden in .dev.vars
+              // so let's mask it
+              maskedVars[key] = "(hidden)";
+            }
           }
-          usageModel={config.usage_model}
-          bindings={bindings}
-          crons={config.triggers.crons}
-        />
-      );
-      await waitUntilExit();
+
+          printBindings({
+            ...bindings,
+            vars: maskedVars,
+          });
+
+          return (
+            <Dev
+              name={getScriptName(args, config)}
+              entry={entry}
+              env={args.env}
+              zone={zoneId}
+              host={host}
+              rules={getRules(config)}
+              legacyEnv={isLegacyEnv(config)}
+              minify={args.minify ?? config.minify}
+              nodeCompat={nodeCompat}
+              build={config.build || {}}
+              initialMode={args.local ? "local" : "remote"}
+              jsxFactory={args["jsx-factory"] || config.jsx_factory}
+              jsxFragment={args["jsx-fragment"] || config.jsx_fragment}
+              tsconfig={args.tsconfig ?? config.tsconfig}
+              upstreamProtocol={upstreamProtocol}
+              localProtocol={
+                args["local-protocol"] || config.dev.local_protocol
+              }
+              enableLocalPersistence={
+                args["experimental-enable-local-persistence"] || false
+              }
+              accountId={config.account_id}
+              assetPaths={getAssetPaths(
+                config,
+                args.site,
+                args.siteInclude,
+                args.siteExclude
+              )}
+              port={args.port || config.dev.port || (await getLocalPort())}
+              ip={args.ip || config.dev.ip}
+              inspectorPort={
+                args["inspector-port"] ?? (await getInspectorPort())
+              }
+              public={args["experimental-public"]}
+              compatibilityDate={getDevCompatibilityDate(
+                config,
+                args["compatibility-date"]
+              )}
+              compatibilityFlags={
+                args["compatibility-flags"] || config.compatibility_flags
+              }
+              usageModel={config.usage_model}
+              bindings={bindings}
+              crons={config.triggers.crons}
+            />
+          );
+        }
+        const { waitUntilExit, rerender } = render(
+          await getDevReactElement(config)
+        );
+        await waitUntilExit();
+      } finally {
+        await watcher?.close();
+      }
     }
   );
 
@@ -2801,3 +2834,13 @@ function getDevCompatibilityDate(
   }
   return compatibilityDate ?? currentDate;
 }
+
+/**
+ * Avoiding calling `getPort()` multiple times by memoizing the first result.
+ */
+function memoizeGetPort(defaultPort: number) {
+  let portValue: number;
+  return async () => {
+    return portValue || (portValue = await getPort({ port: defaultPort }));
+  };
+}
diff --git a/packages/wrangler/src/proxy.ts b/packages/wrangler/src/proxy.ts
index 214f913f2d26..a4362be72133 100644
--- a/packages/wrangler/src/proxy.ts
+++ b/packages/wrangler/src/proxy.ts
@@ -100,7 +100,10 @@ export function usePreviewServer({
         .then((server) => {
           setProxy({
             server,
-            terminator: createHttpTerminator({ server }),
+            terminator: createHttpTerminator({
+              server,
+              gracefulTerminationTimeout: 0,
+            }),
           });
         })
         .catch(async (err) => {
@@ -330,7 +333,9 @@ export function usePreviewServer({
       abortController.abort();
       // Running `proxy.server.close()` does not close open connections, preventing the process from exiting.
       // So we use this `terminator` to close all the connections and force the server to shutdown.
-      proxy.terminator.terminate();
+      proxy.terminator
+        .terminate()
+        .catch(() => logger.error("Failed to terminate the proxy server."));
     };
   }, [port, ip, proxy, localProtocol]);
 }
@@ -450,16 +455,24 @@ export async function waitForPortToBeAvailable(
       // trying to make a server listen on that port, and retrying
       // until it succeeds.
       const server = createHttpServer();
+      const terminator = createHttpTerminator({
+        server,
+        gracefulTerminationTimeout: 0, // default 1000
+      });
+
       server.on("error", (err) => {
         // @ts-expect-error non standard property on Error
         if (err.code !== "EADDRINUSE") {
           doReject(err);
         }
       });
-      server.listen(port, () => {
-        server.close();
-        doResolve();
-      });
+      server.listen(port, () =>
+        terminator
+          .terminate()
+          .then(doResolve, () =>
+            logger.error("Failed to terminate the port checker.")
+          )
+      );
     }
   });
 }