diff --git a/.changeset/grumpy-dolphins-explain.md b/.changeset/grumpy-dolphins-explain.md
new file mode 100644
index 000000000000..48c2440cd225
--- /dev/null
+++ b/.changeset/grumpy-dolphins-explain.md
@@ -0,0 +1,7 @@
+---
+"wrangler": patch
+---
+
+fix: trim trailing whitespace from the secrets before uploading
+
+resolves #993
diff --git a/packages/wrangler/src/__tests__/secret.test.ts b/packages/wrangler/src/__tests__/secret.test.ts
index fd4409149265..81b867cd1de2 100644
--- a/packages/wrangler/src/__tests__/secret.test.ts
+++ b/packages/wrangler/src/__tests__/secret.test.ts
@@ -60,6 +60,22 @@ describe("wrangler secret", () => {
     describe("interactive", () => {
       useMockStdin({ isTTY: true });
 
+      it("should trim stdin secret value", async () => {
+        mockPrompt({
+          text: "Enter a secret value:",
+          type: "password",
+          result: `hunter2
+          `,
+        });
+
+        mockPutRequest({ name: `secret-name`, text: `hunter2` });
+        await runWrangler("secret put secret-name --name script-name");
+        expect(std.out).toMatchInlineSnapshot(`
+          "🌀 Creating the secret for script script-name
+          ✨ Success! Uploaded secret secret-name"
+        `);
+      });
+
       it("should create a secret", async () => {
         mockPrompt({
           text: "Enter a secret value:",
@@ -146,6 +162,25 @@ describe("wrangler secret", () => {
     describe("non-interactive", () => {
       const mockStdIn = useMockStdin({ isTTY: false });
 
+      it("should trim stdin secret value, from piped input", async () => {
+        mockPutRequest({ name: "the-key", text: "the-secret" });
+        // Pipe the secret in as three chunks to test that we reconstitute it correctly.
+        mockStdIn.send(
+          `the`,
+          `-`,
+          `secret
+          ` // whitespace & newline being removed
+        );
+        await runWrangler("secret put the-key --name script-name");
+
+        expect(std.out).toMatchInlineSnapshot(`
+          "🌀 Creating the secret for script script-name
+          ✨ Success! Uploaded secret the-key"
+        `);
+        expect(std.warn).toMatchInlineSnapshot(`""`);
+        expect(std.err).toMatchInlineSnapshot(`""`);
+      });
+
       it("should create a secret, from piped input", async () => {
         mockPutRequest({ name: "the-key", text: "the-secret" });
         // Pipe the secret in as three chunks to test that we reconstitute it correctly.
diff --git a/packages/wrangler/src/index.tsx b/packages/wrangler/src/index.tsx
index 9cc29d816ac2..28a347b37d57 100644
--- a/packages/wrangler/src/index.tsx
+++ b/packages/wrangler/src/index.tsx
@@ -206,6 +206,14 @@ function demandOneOfOption(...options: string[]) {
   };
 }
 
+/**
+ * Remove trailing white space from inputs.
+ * Matching Wrangler legacy behavior with handling inputs
+ */
+function trimTrailingWhitespace(str: string) {
+  return str.trimEnd();
+}
+
 class CommandLineArgsError extends Error {}
 
 function createCLIParser(argv: string[]) {
@@ -1719,9 +1727,11 @@ function createCLIParser(argv: string[]) {
             const accountId = await requireAuth(config);
 
             const isInteractive = process.stdin.isTTY;
-            const secretValue = isInteractive
-              ? await prompt("Enter a secret value:", "password")
-              : await readFromStdin();
+            const secretValue = trimTrailingWhitespace(
+              isInteractive
+                ? await prompt("Enter a secret value:", "password")
+                : await readFromStdin()
+            );
 
             logger.log(
               `🌀 Creating the secret for script ${scriptName} ${