diff --git a/cli/source/app.tsx b/cli/source/app.tsx
index cc3a7a93f..589a5ca7b 100644
--- a/cli/source/app.tsx
+++ b/cli/source/app.tsx
@@ -21,6 +21,7 @@ import { useSelector, store, useDispatch } from './store/index.js';
 import { getLineLimit } from './utils/line-limit.js';
 import { runCommand } from './utils/run-command.js';
 import CircularBuffer from './utils/circularBuffer.js';
+import { isLocalBranchBehindRemote } from './utils/update-checker.js';
 
 const CliUi = () => {
   const dispatch = useDispatch();
@@ -32,6 +33,7 @@ const CliUi = () => {
   useLogsFromAllSources();
 
   const [retryToggle, setRetryToggle] = useState<Boolean>(false);
+  const [isUpdateAvailable, setIsUpdateAvailable] = useState<string>("");
 
   const { exit } = useApp();
 
@@ -90,6 +92,12 @@ const CliUi = () => {
     }, 200);
   }, [dispatch, runCommandOpts]);
 
+  const handleVersionUpdates = useCallback(async () => {
+    await isLocalBranchBehindRemote().then((res) => {
+      setIsUpdateAvailable(res);
+    });
+  }, [setIsUpdateAvailable]);
+
   useEffect(() => {
     if (appState !== AppStates.TERMINATED) return;
     exit();
@@ -119,6 +127,10 @@ const CliUi = () => {
     }
   });
 
+  useEffect(() => {
+    handleVersionUpdates();
+  }, [handleVersionUpdates]);
+
   useEffect(() => {
     const { process, promise } = runCommand(
       'docker-compose',
@@ -347,6 +359,13 @@ const CliUi = () => {
                       </Text>{' '}
                       exit
                     </Text>
+                    {Boolean(isUpdateAvailable) && (
+                      <>
+                        <Text bold color="yellow">
+                          {isUpdateAvailable}
+                        </Text>
+                      </>
+                    )}
                   </Box>
                 );
               case AppStates.TEARDOWN:
diff --git a/cli/source/utils/update-checker.ts b/cli/source/utils/update-checker.ts
new file mode 100644
index 000000000..45d55e13a
--- /dev/null
+++ b/cli/source/utils/update-checker.ts
@@ -0,0 +1,42 @@
+import { execSync } from 'child_process';
+
+const defaultBranch = 'main';
+
+const fetchRemoteRepository = () => {
+  try {
+    execSync('git fetch origin');
+  } catch (error) {
+    console.error(`Error fetching the remote repository: ${error}`);
+  }
+};
+
+const getLatestLocalCommitSHA = () => {
+  fetchRemoteRepository();
+  const commitSHA = execSync(`git rev-parse ${defaultBranch}`)
+    .toString()
+    .trim();
+  return commitSHA;
+};
+
+export async function isLocalBranchBehindRemote(): Promise<string> {
+  const latestLocalCommitSHA = getLatestLocalCommitSHA();
+
+  const behindCommits = execSync(
+    `git rev-list ${latestLocalCommitSHA}..origin/main`
+  )
+    .toString()
+    .trim()
+    .split('\n');
+
+  const behindCommitsCount = behindCommits.filter((commit) => commit).length;
+
+  if (behindCommitsCount == 0) {
+    return '';
+  }
+
+  if (behindCommitsCount == 1) {
+    return `(1 commit behind remote. pull and rebase)`;
+  }
+
+  return `(${behindCommitsCount} commits behind remote. pull and rebase)`;
+}
diff --git a/dev.sh b/dev.sh
index 473ad8bff..8cc15f298 100755
--- a/dev.sh
+++ b/dev.sh
@@ -4,16 +4,42 @@ docker-compose down
 
 cat env.example > .env
 
+check_internet_connection() {
+  curl -s https://www.google.com > /dev/null 2>&1
+  if [[ $? -ne 0 ]]; then
+    echo "No internet connection. Cannot fetch latest commits."
+    return 1
+  fi
+  return 0
+}
+
+if ! check_internet_connection; then
+  BEHIND_COMMITS_COUNT=0
+else
+  git fetch origin
+  BEHIND_COMMITS_COUNT=$(git rev-list --count main..origin/main)
+fi
+
 GIT_COMMIT_HASH=$(git rev-parse main)
 GIT_COMMIT_DATE=$(git show -s --format=%cI $MERGE_COMMIT_SHA)
 
-if [[ "$OSTYPE" == "darwin"* ]]; then
-    sed -i '' "s/^BUILD_DATE=.*/BUILD_DATE=$GIT_COMMIT_DATE/" .env
-    sed -i '' "s/^MERGE_COMMIT_SHA=.*/MERGE_COMMIT_SHA=$GIT_COMMIT_HASH/" .env
-else
-    sed -i "s/^BUILD_DATE=.*/BUILD_DATE=$GIT_COMMIT_DATE/" .env
-    sed -i "s/^MERGE_COMMIT_SHA=.*/MERGE_COMMIT_SHA=$GIT_COMMIT_HASH/" .env
-fi
+update_or_add_env_var() {
+  local var_name=$1
+  local var_value=$2
+  if grep -q "^$var_name=" .env; then
+    if [[ "$OSTYPE" == "darwin"* ]]; then
+      sed -i '' "s/^$var_name=.*/$var_name=$var_value/" .env
+    else
+      sed -i "s/^$var_name=.*/$var_name=$var_value/" .env
+    fi
+  else
+    echo "$var_name=$var_value" >> .env
+  fi
+}
+
+update_or_add_env_var "BUILD_DATE" "$GIT_COMMIT_DATE"
+update_or_add_env_var "MERGE_COMMIT_SHA" "$GIT_COMMIT_HASH"
+update_or_add_env_var "BEHIND_COMMITS_COUNT" "$BEHIND_COMMITS_COUNT"
 
 
 cd ./cli || exit
diff --git a/web-server/libdefs/ambient.d.ts b/web-server/libdefs/ambient.d.ts
index 994fa6caa..a548d8f81 100644
--- a/web-server/libdefs/ambient.d.ts
+++ b/web-server/libdefs/ambient.d.ts
@@ -84,5 +84,6 @@ declare namespace NodeJS {
     DB_USER: string;
     MERGE_COMMIT_SHA: string;
     BUILD_DATE: string;
+    BEHIND_COMMITS_COUNT?: string
   }
 }
diff --git a/web-server/pages/api/internal/version.ts b/web-server/pages/api/internal/version.ts
index 12ceab77e..1fbcc91a1 100644
--- a/web-server/pages/api/internal/version.ts
+++ b/web-server/pages/api/internal/version.ts
@@ -4,6 +4,7 @@ import axios from 'axios';
 const dockerRepoName = 'middlewareeng/middleware';
 const githubOrgName = 'middlewarehq';
 const githubRepoName = 'middleware';
+const defaultBranch = 'main';
 
 const endpoint = new Endpoint(nullSchema);
 
@@ -105,26 +106,26 @@ async function fetchDockerHubTags(): Promise<TagCompressed[]> {
 }
 
 async function fetchLatestGitHubCommit(): Promise<GitHubCommit> {
-  const apiUrl = `https://api.github.com/repos/${githubOrgName}/${githubRepoName}/commits`;
-  const response = await axios.get<GitHubCommit[]>(apiUrl);
-  const latestCommit = response.data[0];
+  const apiUrl = `https://api.github.com/repos/${githubOrgName}/${githubRepoName}/commits/${defaultBranch}`;
+  const response = await axios.get<GitHubCommit>(apiUrl);
+  const latestCommit = response.data;
   return latestCommit;
 }
 
-function isUpdateAvailable(
-  localVersionInfo: ProjectVersionInfo,
-  dockerLatestRemoteTag: TagCompressed,
-  githubLatestCommit: GitHubCommit
-): boolean {
+function isUpdateAvailable({
+  localVersionInfo,
+  dockerLatestRemoteTag
+}: {
+  localVersionInfo: ProjectVersionInfo;
+  dockerLatestRemoteTag: TagCompressed;
+}): boolean {
   const env = process.env.NEXT_PUBLIC_APP_ENVIRONMENT;
 
   if (env == 'development') {
-    const localBuildDate = new Date(localVersionInfo.current_build_date);
-    const latestRemoteCommitDate = new Date(
-      githubLatestCommit.commit.author.date
-    );
-
-    return latestRemoteCommitDate > localBuildDate;
+    const behindCommitsCount = process.env.BEHIND_COMMITS_COUNT
+      ? Number(process.env.BEHIND_COMMITS_COUNT)
+      : 0;
+    return behindCommitsCount > 0;
   }
 
   const localBuildDate = new Date(localVersionInfo.current_build_date);
@@ -156,11 +157,10 @@ async function checkNewImageRelease(): Promise<CheckNewVersionResponse> {
     latest_docker_image: latestDockerImageLink,
     github_repo: githubRepLink,
     current_github_commit: versionInfo.merge_commit_sha,
-    is_update_available: isUpdateAvailable(
-      versionInfo,
-      latestTag,
-      githubLatestCommit
-    ),
+    is_update_available: isUpdateAvailable({
+      dockerLatestRemoteTag: latestTag,
+      localVersionInfo: versionInfo
+    }),
     latest_docker_image_build_date: latestRemoteDate
   };
 }