diff --git a/src/cli.ts b/src/cli.ts
index 0046ee92..f913c0f3 100644
--- a/src/cli.ts
+++ b/src/cli.ts
@@ -24,6 +24,10 @@ async function main(argv: string[]) {
       "Request headers to redact",
       commaSeparatedList
     )
+    .option(
+      "--no-drop-conditional-request-headers",
+      "When running in record mode, by default, `If-*` headers from outgoing requests are dropped in an attempt to prevent the suite of conditional responses being returned (e.g. 304). Supplying this flag disables this default behaviour"
+    )
     .parse(argv);
 
   const initialMode: string = (program.mode || "").toLowerCase();
@@ -32,6 +36,7 @@ async function main(argv: string[]) {
   const host: string = program.host;
   const port = parseInt(program.port, 10);
   const redactHeaders: string[] = program.redactHeaders;
+  const preventConditionalRequests: boolean = !!program.dropConditionalRequestHeaders;
 
   switch (initialMode) {
     case "record":
@@ -55,6 +60,12 @@ async function main(argv: string[]) {
     );
   }
 
+  if (preventConditionalRequests && initialMode === "record") {
+    console.info(
+      "The prevent conditional requests flag is enabled in record mode. All received `If-*` headers will not be forwarded on upstream and will not be recorded in tapes."
+    );
+  }
+
   // Expect a host unless we're in replay mode.
   if (initialMode !== "replay") {
     if (!host) {
@@ -72,6 +83,7 @@ async function main(argv: string[]) {
     defaultTapeName,
     enableLogging: true,
     redactHeaders,
+    preventConditionalRequests,
   });
   await server.start(port);
   console.log(chalk.green(`Proxying in ${initialMode} mode on port ${port}.`));
diff --git a/src/server.ts b/src/server.ts
index 8c68216a..1875d905 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -23,6 +23,7 @@ export class RecordReplayServer {
   private loggingEnabled: boolean;
   private defaultTape: string;
   private replayedTapes: Set<TapeRecord> = new Set();
+  private preventConditionalRequests?: boolean;
 
   constructor(options: {
     initialMode: Mode;
@@ -32,6 +33,7 @@ export class RecordReplayServer {
     timeout?: number;
     enableLogging?: boolean;
     redactHeaders?: string[];
+    preventConditionalRequests?: boolean;
   }) {
     this.currentTapeRecords = [];
     this.mode = options.initialMode;
@@ -41,6 +43,7 @@ export class RecordReplayServer {
     const redactHeaders = options.redactHeaders || [];
     this.persistence = new Persistence(options.tapeDir, redactHeaders);
     this.defaultTape = options.defaultTapeName;
+    this.preventConditionalRequests = options.preventConditionalRequests;
     this.loadTape(this.defaultTape);
 
     this.server = http.createServer(async (req, res) => {
@@ -57,6 +60,15 @@ export class RecordReplayServer {
         return;
       }
 
+      if (
+        this.preventConditionalRequests &&
+        (req.method === "GET" || req.method === "HEAD")
+      ) {
+        // Headers are always coming in as lowercase.
+        delete req.headers["if-modified-since"];
+        delete req.headers["if-none-match"];
+      }
+
       try {
         const request: Request = {
           method: req.method,