diff --git a/__tests__/commands/pages/__snapshots__/upload.test.ts.snap b/__tests__/commands/pages/__snapshots__/upload.test.ts.snap
index 3985ae746..dd8a9c1c5 100644
--- a/__tests__/commands/pages/__snapshots__/upload.test.ts.snap
+++ b/__tests__/commands/pages/__snapshots__/upload.test.ts.snap
@@ -822,6 +822,20 @@ exports[`rdme docs upload > given that the file path is a single file > should e
 }
 `;
 
+exports[`rdme docs upload > given that the file path is a single file > should gracefully handle errors that claim they are JSON but are not 1`] = `
+{
+  "error": [Error: The ReadMe API responded with an unexpected error. Please try again and if this issue persists, get in touch with us at support@readme.io.],
+  "stderr": "- 🔬 Validating frontmatter data...
+✔ 🔬 Validating frontmatter data... no issues found!
+- 🚀 Uploading files to ReadMe...
+✖ 🚀 Uploading files to ReadMe... 1 file(s) failed.
+",
+  "stdout": "🚨 Received errors when attempting to upload 1 page(s):
+   - __tests__/__fixtures__/docs/new-docs/new-doc.md: The ReadMe API responded with an unexpected error. Please try again and if this issue persists, get in touch with us at support@readme.io.
+",
+}
+`;
+
 exports[`rdme docs upload > given that the file path is a single file > should not throw an error if \`max-errors\` flag is set to -1 1`] = `
 {
   "result": {
@@ -1672,6 +1686,20 @@ exports[`rdme reference upload > given that the file path is a single file > sho
 }
 `;
 
+exports[`rdme reference upload > given that the file path is a single file > should gracefully handle errors that claim they are JSON but are not 1`] = `
+{
+  "error": [Error: The ReadMe API responded with an unexpected error. Please try again and if this issue persists, get in touch with us at support@readme.io.],
+  "stderr": "- 🔬 Validating frontmatter data...
+✔ 🔬 Validating frontmatter data... no issues found!
+- 🚀 Uploading files to ReadMe...
+✖ 🚀 Uploading files to ReadMe... 1 file(s) failed.
+",
+  "stdout": "🚨 Received errors when attempting to upload 1 page(s):
+   - __tests__/__fixtures__/docs/new-docs/new-doc.md: The ReadMe API responded with an unexpected error. Please try again and if this issue persists, get in touch with us at support@readme.io.
+",
+}
+`;
+
 exports[`rdme reference upload > given that the file path is a single file > should not throw an error if \`max-errors\` flag is set to -1 1`] = `
 {
   "result": {
diff --git a/__tests__/commands/pages/upload.test.ts b/__tests__/commands/pages/upload.test.ts
index d3a93fcdd..5b0dba6bb 100644
--- a/__tests__/commands/pages/upload.test.ts
+++ b/__tests__/commands/pages/upload.test.ts
@@ -104,6 +104,26 @@ describe.each([
       mock.done();
     });
 
+    it('should gracefully handle errors that claim they are JSON but are not', async () => {
+      const mock = getAPIv2Mock({ authorization })
+        .get(`/branches/stable/${route}/new-doc`)
+        .reply(404)
+        .post(`/branches/stable/${route}`, {
+          category: { uri: `/branches/stable/categories/${route}/category-slug` },
+          slug: 'new-doc',
+          title: 'This is the document title',
+          content: { body: '\nBody\n' },
+        })
+        .reply(201, '<>yikes</>', { 'content-type': 'application/json' });
+
+      const result = await run(['__tests__/__fixtures__/docs/new-docs/new-doc.md', '--key', key]);
+
+      expect(result).toMatchSnapshot();
+      expect(fs.writeFileSync).not.toHaveBeenCalled();
+
+      mock.done();
+    });
+
     describe('given that the --dry-run flag is passed', () => {
       it('should not create anything in ReadMe', async () => {
         const mock = getAPIv2Mock({ authorization }).get(`/branches/stable/${route}/new-doc`).reply(404);
diff --git a/src/lib/readmeAPIFetch.ts b/src/lib/readmeAPIFetch.ts
index 405e241e6..303ebf549 100644
--- a/src/lib/readmeAPIFetch.ts
+++ b/src/lib/readmeAPIFetch.ts
@@ -348,15 +348,27 @@ export async function handleAPIv1Res(
 ) {
   const contentType = res.headers.get('content-type') || '';
   const extension = mime.extension(contentType);
+  debug(`received status code ${res.status} from ${res.url} with content type: ${contentType}`);
   if (extension === 'json') {
-    // TODO: type this better
-    // biome-ignore lint/suspicious/noExplicitAny: We do not have TS types for APIv1 responses.
-    const body = (await res.json()) as any;
-    debug(`received status code ${res.status} from ${res.url} with JSON response: ${JSON.stringify(body)}`);
-    if (body.error && rejectOnJsonError) {
-      return Promise.reject(new APIv1Error(body));
+    // Just to be safe, we parse the response as text first in case the response is not valid JSON.
+    const text = await res.text();
+    debug(`received status code ${res.status} from ${res.url} with JSON response: ${text}`);
+    try {
+      // biome-ignore lint/suspicious/noExplicitAny: We do not have TS types for APIv1 responses.
+      const body = JSON.parse(text) as any;
+      if (body.error && rejectOnJsonError) {
+        throw new APIv1Error(body);
+      }
+      return body;
+    } catch (e) {
+      if (e instanceof APIv1Error) {
+        throw e;
+      }
+      debug(`received the following error when attempting to parse JSON response: ${e.message}`);
+      throw new Error(
+        'The ReadMe API responded with an unexpected error. Please try again and if this issue persists, get in touch with us at support@readme.io.',
+      );
     }
-    return body;
   }
   if (res.status === SUCCESS_NO_CONTENT) {
     debug(`received status code ${res.status} from ${res.url} with no content`);
@@ -386,6 +398,7 @@ export async function handleAPIv2Res<R extends ResponseBody = ResponseBody, T ex
 ): Promise<R> {
   const contentType = res.headers.get('content-type') || '';
   const extension = mime.extension(contentType) || contentType.includes('json') ? 'json' : false;
+  this.debug(`received status code ${res.status} from ${res.url} with content type: ${contentType}`);
   if (res.status === SUCCESS_NO_CONTENT) {
     // to prevent a memory leak, we should still consume the response body? even though we don't use it?
     // https://x.com/cramforce/status/1762142087930433999
@@ -393,12 +406,24 @@ export async function handleAPIv2Res<R extends ResponseBody = ResponseBody, T ex
     this.debug(`received status code ${res.status} from ${res.url} with no content: ${body}`);
     return {} as R;
   } else if (extension === 'json') {
-    const body = (await res.json()) as R;
-    this.debug(`received status code ${res.status} from ${res.url} with JSON response: ${JSON.stringify(body)}`);
-    if (!res.ok) {
-      throw new APIv2Error(body as APIv2ErrorResponse);
+    // Just to be safe, we parse the response as text first in case the response is not valid JSON.
+    const text = await res.text();
+    this.debug(`received status code ${res.status} from ${res.url} with JSON response: ${text}`);
+    try {
+      const body = JSON.parse(text) as R;
+      if (!res.ok) {
+        throw new APIv2Error(body as APIv2ErrorResponse);
+      }
+      return body;
+    } catch (e) {
+      if (e instanceof APIv2Error) {
+        throw e;
+      }
+      this.debug(`received the following error when attempting to parse JSON response: ${e.message}`);
+      throw new Error(
+        'The ReadMe API responded with an unexpected error. Please try again and if this issue persists, get in touch with us at support@readme.io.',
+      );
     }
-    return body;
   }
 
   // If we receive a non-JSON response, it's likely an error.