diff --git a/system/src/Grav/Console/Gpm/SelfupgradeCommand.php b/system/src/Grav/Console/Gpm/SelfupgradeCommand.php
index c52fd5290..7c7a5b63b 100644
--- a/system/src/Grav/Console/Gpm/SelfupgradeCommand.php
+++ b/system/src/Grav/Console/Gpm/SelfupgradeCommand.php
@@ -232,6 +232,29 @@ class SelfupgradeCommand extends GpmCommand
             $io->writeln("Grav v<cyan>{$remote}</cyan> is now available [release date: {$release}].");
             $io->writeln('You are currently using v<cyan>' . GRAV_VERSION . '</cyan>.');
 
+            // Determine if this is a major/minor version upgrade
+            $localParts = explode('.', $local);
+            $remoteParts = explode('.', $remote);
+
+            $localMajor = (int)($localParts[0] ?? 0);
+            $localMinor = (int)($localParts[1] ?? 0);
+            $remoteMajor = (int)($remoteParts[0] ?? 0);
+            $remoteMinor = (int)($remoteParts[1] ?? 0);
+
+            // Check if this is a major/minor version change (e.g., 1.7.x -> 1.8.y)
+            $isMajorMinorUpgrade = ($localMajor !== $remoteMajor) || ($localMinor !== $remoteMinor);
+
+            if ($isMajorMinorUpgrade) {
+                $io->newLine();
+                $io->writeln('<yellow>NOTE</yellow>: This is a major version upgrade.');
+                $io->writeln('It is recommended to run `<cyan>bin/gpm update</cyan>` first to update all plugins and themes');
+                $io->writeln('to their latest compatible versions before upgrading Grav core.');
+            } else {
+                $io->newLine();
+                $io->writeln('<green>NOTE</green>: This is a patch version upgrade.');
+                $io->writeln('You can safely proceed. Grav will check for any plugin compatibility issues during the upgrade.');
+            }
+
             if (!$this->all_yes) {
                 $question = new ConfirmationQuestion(
                     'Would you like to read the changelog before proceeding? [y|N] ',
diff --git a/system/src/Grav/Console/Gpm/UpdateCommand.php b/system/src/Grav/Console/Gpm/UpdateCommand.php
index 143500c08..b7b4e8b8f 100644
--- a/system/src/Grav/Console/Gpm/UpdateCommand.php
+++ b/system/src/Grav/Console/Gpm/UpdateCommand.php
@@ -117,15 +117,38 @@ class UpdateCommand extends GpmCommand
         $local = $this->upgrader->getLocalVersion();
         $remote = $this->upgrader->getRemoteVersion();
         if ($local !== $remote) {
-            $io->writeln('<yellow>WARNING</yellow>: A new version of Grav is available. You should update Grav before updating plugins and themes. If you continue without updating Grav, some plugins or themes may stop working.');
-            $io->newLine();
-            $question = new ConfirmationQuestion('Continue with the update process? [Y|n] ', true);
-            $answer = $io->askQuestion($question);
+            // Determine if this is a major/minor version upgrade by comparing versions
+            $localParts = explode('.', $local);
+            $remoteParts = explode('.', $remote);
 
-            if (!$answer) {
-                $io->writeln('<red>Update aborted. Exiting...</red>');
+            $localMajor = (int)($localParts[0] ?? 0);
+            $localMinor = (int)($localParts[1] ?? 0);
+            $remoteMajor = (int)($remoteParts[0] ?? 0);
+            $remoteMinor = (int)($remoteParts[1] ?? 0);
 
-                return 1;
+            // Check if this is a major/minor version change (e.g., 1.7.x -> 1.8.y)
+            $isMajorMinorUpgrade = ($localMajor !== $remoteMajor) || ($localMinor !== $remoteMinor);
+
+            if ($isMajorMinorUpgrade) {
+                // For major/minor upgrades (e.g., 1.7.x -> 1.8.y), recommend updating plugins FIRST
+                $io->writeln('<yellow>WARNING</yellow>: A new major version of Grav is available (v' . $local . ' -> v' . $remote . ').');
+                $io->writeln('For major version upgrades, you should update plugins and themes to their latest compatible versions BEFORE upgrading Grav core.');
+                $io->writeln('This ensures plugins have any necessary compatibility fixes for the new Grav version.');
+                $io->newLine();
+                $io->writeln('<green>It is recommended to proceed with updating plugins and themes now.</green>');
+            } else {
+                // For patch upgrades (e.g., 1.7.45 -> 1.7.46), recommend updating Grav FIRST
+                $io->writeln('<yellow>WARNING</yellow>: A new version of Grav is available (v' . $local . ' -> v' . $remote . ').');
+                $io->writeln('You should update Grav before updating plugins and themes. If you continue without updating Grav, some plugins or themes may stop working.');
+                $io->newLine();
+                $question = new ConfirmationQuestion('Continue with the update process? [Y|n] ', true);
+                $answer = $io->askQuestion($question);
+
+                if (!$answer) {
+                    $io->writeln('<red>Update aborted. Exiting...</red>');
+
+                    return 1;
+                }
             }
         }