diff --git a/bin/typedoc b/bin/typedoc
index 4a26d5636..dad5e7ed1 100755
--- a/bin/typedoc
+++ b/bin/typedoc
@@ -58,6 +58,24 @@ async function run(app) {
         return ExitCodes.NoEntryPoints;
     }
 
+    if (app.options.getValue("watch")) {
+        app.convertAndWatch(async (project) => {
+            const out = app.options.getValue("out");
+            if (out) {
+                await app.generateDocs(project, out);
+            }
+            const json = app.options.getValue("json");
+            if (json) {
+                await app.generateJson(project, json);
+            }
+
+            if (!out && !json) {
+                await app.generateDocs(project, "./docs");
+            }
+        });
+        return ExitCodes.Ok;
+    }
+
     const project = app.convert();
     if (!project) {
         return ExitCodes.CompileError;
diff --git a/src/lib/application.ts b/src/lib/application.ts
index 437aa052c..5f6493154 100644
--- a/src/lib/application.ts
+++ b/src/lib/application.ts
@@ -24,6 +24,7 @@ import {
 import { Options, BindOption } from "./utils";
 import { TypeDocOptions } from "./utils/options/declaration";
 import { flatMap } from "./utils/array";
+import { basename } from "path";
 
 // eslint-disable-next-line @typescript-eslint/no-var-requires
 const packageInfo = require("../../package.json") as {
@@ -238,12 +239,133 @@ export class Application extends ChildableComponent<
             return;
         }
 
+        if (this.application.options.getValue("emit")) {
+            for (const program of programs) {
+                program.emit();
+            }
+        }
+
         return this.converter.convert(
             this.expandInputFiles(this.entryPoints),
             programs
         );
     }
 
+    public convertAndWatch(
+        success: (project: ProjectReflection) => Promise<void>
+    ): void {
+        if (
+            !this.options.getValue("preserveWatchOutput") &&
+            this.logger instanceof ConsoleLogger
+        ) {
+            ts.sys.clearScreen?.();
+        }
+
+        this.logger.verbose(
+            "Using TypeScript %s from %s",
+            this.getTypeScriptVersion(),
+            this.getTypeScriptPath()
+        );
+
+        if (
+            !supportedVersionMajorMinor.some(
+                (version) => version == ts.versionMajorMinor
+            )
+        ) {
+            this.logger.warn(
+                `You are running with an unsupported TypeScript version! TypeDoc supports ${supportedVersionMajorMinor.join(
+                    ", "
+                )}`
+            );
+        }
+
+        if (Object.keys(this.options.getCompilerOptions()).length === 0) {
+            this.logger.warn(
+                `No compiler options set. This likely means that TypeDoc did not find your tsconfig.json. Generated documentation will probably be empty.`
+            );
+        }
+
+        // Doing this is considerably more complicated, we'd need to manage an array of programs, not convert until all programs
+        // have reported in the first time... just error out for now. I'm not convinced anyone will actually notice.
+        if (this.application.options.getFileNames().length === 0) {
+            this.logger.error(
+                "The provided tsconfig file looks like a solution style tsconfig, which is not supported in watch mode."
+            );
+            return;
+        }
+
+        // Matches the behavior of the tsconfig option reader.
+        let tsconfigFile = this.options.getValue("tsconfig");
+        tsconfigFile =
+            ts.findConfigFile(
+                tsconfigFile,
+                ts.sys.fileExists,
+                tsconfigFile.toLowerCase().endsWith(".json")
+                    ? basename(tsconfigFile)
+                    : undefined
+            ) ?? "tsconfig.json";
+
+        // We don't want to do it the first time to preserve initial debug status messages. They'll be lost
+        // after the user saves a file, but better than nothing...
+        let firstStatusReport = true;
+
+        const host = ts.createWatchCompilerHost(
+            tsconfigFile,
+            { noEmit: !this.application.options.getValue("emit") },
+            ts.sys,
+            ts.createEmitAndSemanticDiagnosticsBuilderProgram,
+            (diagnostic) => this.logger.diagnostic(diagnostic),
+            (status, newLine, _options, errorCount) => {
+                if (
+                    !firstStatusReport &&
+                    errorCount === void 0 &&
+                    !this.options.getValue("preserveWatchOutput") &&
+                    this.logger instanceof ConsoleLogger
+                ) {
+                    ts.sys.clearScreen?.();
+                }
+                firstStatusReport = false;
+                this.logger.write(
+                    ts.flattenDiagnosticMessageText(status.messageText, newLine)
+                );
+            }
+        );
+
+        let successFinished = true;
+        let currentProgram: ts.Program | undefined;
+
+        const runSuccess = () => {
+            if (!currentProgram) {
+                return;
+            }
+
+            if (successFinished) {
+                this.logger.resetErrors();
+                const project = this.converter.convert(
+                    this.expandInputFiles(this.entryPoints),
+                    currentProgram
+                );
+                currentProgram = undefined;
+                successFinished = false;
+                success(project).then(() => {
+                    successFinished = true;
+                    runSuccess();
+                });
+            }
+        };
+
+        const origAfterProgramCreate = host.afterProgramCreate;
+        host.afterProgramCreate = (program) => {
+            if (ts.getPreEmitDiagnostics(program.getProgram()).length === 0) {
+                currentProgram = program.getProgram();
+                runSuccess();
+            }
+            origAfterProgramCreate?.(program);
+        };
+
+        ts.createWatchProgram(host);
+    }
+
     /**
      * Render HTML for the given project
      */
diff --git a/src/lib/converter/converter.ts b/src/lib/converter/converter.ts
index 9eaf97525..7ab0d5025 100644
--- a/src/lib/converter/converter.ts
+++ b/src/lib/converter/converter.ts
@@ -139,7 +139,7 @@ export class Converter extends ChildableComponent<
     convert(
         entryPoints: readonly string[],
         programs: ts.Program | readonly ts.Program[]
-    ): ProjectReflection | undefined {
+    ): ProjectReflection {
         programs = programs instanceof Array ? programs : [programs];
         this.externalPatternCache = void 0;
 
diff --git a/src/lib/utils/options/declaration.ts b/src/lib/utils/options/declaration.ts
index c182cdcd9..671ea192b 100644
--- a/src/lib/utils/options/declaration.ts
+++ b/src/lib/utils/options/declaration.ts
@@ -48,6 +48,10 @@ export interface TypeDocOptionMap {
     includes: string;
     media: string;
 
+    emit: boolean;
+    watch: boolean;
+    preserveWatchOutput: boolean;
+
     out: string;
     json: string;
 
diff --git a/src/lib/utils/options/readers/arguments.ts b/src/lib/utils/options/readers/arguments.ts
index 52e1548e0..75845f5a8 100644
--- a/src/lib/utils/options/readers/arguments.ts
+++ b/src/lib/utils/options/readers/arguments.ts
@@ -16,10 +16,6 @@ export class ArgumentsReader implements OptionsReader {
     }
 
     read(container: Options, logger: Logger): void {
-        logger.verbose(
-            `Arguments reader reading with: ${JSON.stringify(this.args)}`
-        );
-
         // Make container's type more lax, we do the appropriate checks manually.
         const options = container as Options & {
             setValue(name: string, value: unknown): void;
diff --git a/src/lib/utils/options/sources/typedoc.ts b/src/lib/utils/options/sources/typedoc.ts
index 68ea095fd..cd848660b 100644
--- a/src/lib/utils/options/sources/typedoc.ts
+++ b/src/lib/utils/options/sources/typedoc.ts
@@ -84,6 +84,23 @@ export function addTypeDocOptions(options: Pick<Options, "addDeclaration">) {
         hint: ParameterHint.Directory,
     });
 
+    options.addDeclaration({
+        name: "watch",
+        help: "Watch files for changes and rebuild docs on change.",
+        type: ParameterType.Boolean,
+    });
+    options.addDeclaration({
+        name: "preserveWatchOutput",
+        help:
+            "If set, TypeDoc will not clear the screen between compilation runs.",
+        type: ParameterType.Boolean,
+    });
+    options.addDeclaration({
+        name: "emit",
+        help: "If set, TypeDoc will emit the TypeScript compilation result",
+        type: ParameterType.Boolean,
+    });
+
     options.addDeclaration({
         name: "out",
         help: "Specifies the location the documentation should be written to.",