diff --git a/package.json b/package.json
index bf9da4a..cccbcb0 100644
--- a/package.json
+++ b/package.json
@@ -88,6 +88,7 @@
     "@types/tar-js": "^0.3.5",
     "axios": "^1.6.2",
     "commander": "^11.1.0",
+    "compare-versions": "^6.1.0",
     "dockerode": "^4.0.2",
     "env-paths": "^2.2.1",
     "formdata-node": "^6.0.3",
diff --git a/src/cli/utils.ts b/src/cli/utils.ts
index e221079..8753a0f 100644
--- a/src/cli/utils.ts
+++ b/src/cli/utils.ts
@@ -9,6 +9,7 @@ import { type Duplex, Writable } from "stream";
 import { fileURLToPath } from "url";
 
 import axios from "axios";
+import { compareVersions } from "compare-versions";
 import Docker from "dockerode";
 import type { Schema } from "jsonschema";
 import nunjucks from "nunjucks";
@@ -494,21 +495,36 @@ export async function getDockerImageTags(
   repository: string,
   username: string = "sindrilabs",
 ): Promise<string[]> {
-  const url = `https://hub.docker.com/v2/repositories/${username}/${repository}/tags/`;
-  const {
-    data: { results },
-  } = await axios.get<{
-    results: Array<{
-      last_updated: string;
-      name: string;
-      tag_status: string;
-    }>;
-  }>(url);
+  let url: string | undefined =
+    `https://hub.docker.com/v2/repositories/${username}/${repository}/tags/?page_size=1`;
+  interface Result {
+    last_updated: string;
+    name: string;
+    tag_status: string;
+  }
+  interface Response {
+    count: number;
+    next?: string;
+    previous: string | null;
+    results: Result[];
+  }
+  let results: Result[] = [];
+
+  while (url) {
+    const response: { data: Response } = await axios.get<Response>(url);
+
+    results = results.concat(response.data.results);
+    url = response.data.next; // Update the URL for the next request, or null if no more pages
+  }
+
   return results
     .filter(({ tag_status }) => tag_status === "active")
     .filter(({ name }) => name !== "dev")
     .sort((a, b) => a.last_updated.localeCompare(b.last_updated))
-    .map(({ name }) => name);
+    .map(({ name }) => name)
+    .sort((a, b) =>
+      a === "latest" ? 1 : b === "latest" ? -1 : compareVersions(a, b),
+    );
 }
 
 /**
diff --git a/yarn.lock b/yarn.lock
index 8b16ae6..fe733aa 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -1670,6 +1670,11 @@ common-path-prefix@^3.0.0:
   resolved "https://registry.npmjs.org/common-path-prefix/-/common-path-prefix-3.0.0.tgz"
   integrity sha512-QE33hToZseCH3jS0qN96O/bSh3kaw/h+Tq7ngyY9eWDUnTlTNUyqfqvCXioLe5Na5jFsL78ra/wuBU4iuEgd4w==
 
+compare-versions@^6.1.0:
+  version "6.1.0"
+  resolved "https://registry.yarnpkg.com/compare-versions/-/compare-versions-6.1.0.tgz#3f2131e3ae93577df111dba133e6db876ffe127a"
+  integrity sha512-LNZQXhqUvqUTotpZ00qLSaify3b4VFD588aRr8MKFw4CMUr98ytzCW5wDH5qx/DEY5kCDXcbcRuCqL0szEf2tg==
+
 concat-map@0.0.1:
   version "0.0.1"
   resolved "https://registry.npmjs.org/concat-map/-/concat-map-0.0.1.tgz"