diff --git a/src/Command/SelfUpdateCommand.php b/src/Command/SelfUpdateCommand.php
index 31ff5798..bc7897ca 100644
--- a/src/Command/SelfUpdateCommand.php
+++ b/src/Command/SelfUpdateCommand.php
@@ -14,6 +14,7 @@
 use Php\Pie\Platform;
 use Php\Pie\SelfManage\Update\Channel;
 use Php\Pie\SelfManage\Update\FetchPieReleaseFromGitHub;
+use Php\Pie\SelfManage\Update\IsBrewInstallation;
 use Php\Pie\SelfManage\Update\ReleaseIsNewer;
 use Php\Pie\SelfManage\Update\ReleaseMetadata;
 use Php\Pie\SelfManage\Verify\FailedToVerifyRelease;
@@ -30,6 +31,8 @@
 use Throwable;
 
 use function file_get_contents;
+use function is_link;
+use function realpath;
 use function sprintf;
 use function unlink;
 
@@ -87,6 +90,15 @@ public function execute(InputInterface $input, OutputInterface $output): int
             return Command::FAILURE;
         }
 
+        $originalPathToSelf = ($this->fullPathToSelf)();
+        $fullPathToSelf     = is_link($originalPathToSelf) ? (realpath($originalPathToSelf) ?: $originalPathToSelf) : $originalPathToSelf;
+
+        if ((new IsBrewInstallation())($fullPathToSelf, $originalPathToSelf)) {
+            $this->io->writeError('<comment>Aborting! PIE was installed with Brew, you should upgrade with `brew upgrade pie`.</comment>');
+
+            return Command::FAILURE;
+        }
+
         $settings      = new Settings(Platform::getPieBaseWorkingDirectory());
         $updateChannel = $settings->updateChannel();
 
@@ -197,7 +209,6 @@ public function execute(InputInterface $input, OutputInterface $output): int
             return Command::FAILURE;
         }
 
-        $fullPathToSelf = ($this->fullPathToSelf)();
         $this->io->write(
             sprintf('Writing new version to %s', $fullPathToSelf),
             verbosity: IOInterface::VERBOSE,
diff --git a/src/SelfManage/Update/IsBrewInstallation.php b/src/SelfManage/Update/IsBrewInstallation.php
new file mode 100644
index 00000000..ab951423
--- /dev/null
+++ b/src/SelfManage/Update/IsBrewInstallation.php
@@ -0,0 +1,19 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Php\Pie\SelfManage\Update;
+
+use function str_contains;
+
+/** @internal This is not public API for PIE, so should not be depended upon unless you accept the risk of BC breaks */
+final class IsBrewInstallation
+{
+    public function __invoke(string $resolvedPath, string $originalPath): bool
+    {
+        return str_contains($resolvedPath, '/usr/local/Cellar')
+            || str_contains($resolvedPath, '/opt/homebrew/Cellar')
+            || str_contains($originalPath, '/usr/local/Cellar')
+            || str_contains($originalPath, '/opt/homebrew/Cellar');
+    }
+}
diff --git a/test/end-to-end/Dockerfile b/test/end-to-end/Dockerfile
index a827bb98..375978f6 100644
--- a/test/end-to-end/Dockerfile
+++ b/test/end-to-end/Dockerfile
@@ -50,7 +50,7 @@ COPY --from=build_pie_phar /app/pie.phar /usr/local/bin/pie
 RUN pie install -v --auto-install-system-dependencies php/sodium
 
 FROM alpine AS test_pie_installs_system_deps_on_alpine
-RUN apk add php php-phar php-mbstring php-iconv php-openssl bzip2-dev libbz2 build-base autoconf bison re2c libtool php84-dev
+RUN apk add php php-phar php-mbstring php-iconv php-openssl bzip2-dev libbz2 build-base autoconf bison re2c libtool php85-dev
 COPY --from=build_pie_phar /app/pie.phar /usr/local/bin/pie
 RUN pie install -v --auto-install-system-dependencies php/sodium
 
diff --git a/test/unit/SelfManage/Update/IsBrewInstallationTest.php b/test/unit/SelfManage/Update/IsBrewInstallationTest.php
new file mode 100644
index 00000000..7c640ae7
--- /dev/null
+++ b/test/unit/SelfManage/Update/IsBrewInstallationTest.php
@@ -0,0 +1,108 @@
+<?php
+
+declare(strict_types=1);
+
+namespace Php\PieUnitTest\SelfManage\Update;
+
+use Composer\Util\Filesystem;
+use Php\Pie\SelfManage\Update\IsBrewInstallation;
+use PHPUnit\Framework\Attributes\CoversClass;
+use PHPUnit\Framework\Attributes\DataProvider;
+use PHPUnit\Framework\Attributes\RequiresOperatingSystemFamily;
+use PHPUnit\Framework\TestCase;
+
+use function mkdir;
+use function realpath;
+use function symlink;
+use function sys_get_temp_dir;
+use function touch;
+use function uniqid;
+
+use const DIRECTORY_SEPARATOR;
+
+#[CoversClass(IsBrewInstallation::class)]
+final class IsBrewInstallationTest extends TestCase
+{
+    /** @return array<non-empty-string, array{0: string, 1: string, 2: bool}> */
+    public static function pathProvider(): array
+    {
+        return [
+            'regular-path'                => ['/home/user/.local/bin/pie.phar', '/home/user/.local/bin/pie.phar', false],
+            'both-regular-usr-local'      => ['/usr/local/bin/pie', '/usr/local/bin/pie', false],
+            'intel-mac-cellar-direct'     => ['/usr/local/Cellar/pie/1.0/bin/pie', '/usr/local/Cellar/pie/1.0/bin/pie', true],
+            'apple-silicon-cellar-direct' => ['/opt/homebrew/Cellar/pie/1.0/bin/pie', '/opt/homebrew/Cellar/pie/1.0/bin/pie', true],
+            'resolved-is-cellar'          => ['/opt/homebrew/Cellar/pie/1.0/bin/pie', '/usr/local/bin/pie', true],
+            'original-is-cellar'          => ['/usr/local/bin/pie', '/opt/homebrew/Cellar/pie/1.0/bin/pie', true],
+        ];
+    }
+
+    #[DataProvider('pathProvider')]
+    public function testIsBrewInstallationWithPaths(
+        string $resolvedPath,
+        string $originalPath,
+        bool $expected,
+    ): void {
+        self::assertSame($expected, (new IsBrewInstallation())($resolvedPath, $originalPath));
+    }
+
+    #[RequiresOperatingSystemFamily('Linux')]
+    public function testSymlinkAtRegularPathPointingIntoBrewCellarIsDetected(): void
+    {
+        $tmpDir      = sys_get_temp_dir() . DIRECTORY_SEPARATOR . uniqid('pie_brew_test_', true);
+        $cellarFile  = $tmpDir . '/opt/homebrew/Cellar/pie/1.0/pie.phar';
+        $symlinkPath = $tmpDir . '/pie';
+
+        mkdir($tmpDir . '/opt/homebrew/Cellar/pie/1.0', 0777, true);
+        touch($cellarFile);
+        symlink($cellarFile, $symlinkPath);
+
+        try {
+            $resolvedPath = realpath($symlinkPath);
+            self::assertIsString($resolvedPath);
+            self::assertTrue((new IsBrewInstallation())($resolvedPath, $symlinkPath));
+        } finally {
+            (new Filesystem())->remove($tmpDir);
+        }
+    }
+
+    #[RequiresOperatingSystemFamily('Linux')]
+    public function testSymlinkAtRegularPathPointingToNonBrewPathIsNotDetected(): void
+    {
+        $tmpDir      = sys_get_temp_dir() . DIRECTORY_SEPARATOR . uniqid('pie_brew_test_', true);
+        $regularFile = $tmpDir . '/regular/pie.phar';
+        $symlinkPath = $tmpDir . '/pie';
+
+        mkdir($tmpDir . '/regular', 0777, true);
+        touch($regularFile);
+        symlink($regularFile, $symlinkPath);
+
+        try {
+            $resolvedPath = realpath($symlinkPath);
+            self::assertIsString($resolvedPath);
+            self::assertFalse((new IsBrewInstallation())($resolvedPath, $symlinkPath));
+        } finally {
+            (new Filesystem())->remove($tmpDir);
+        }
+    }
+
+    #[RequiresOperatingSystemFamily('Linux')]
+    public function testSymlinkInCellarPointingToRegularPathIsDetectedViaOriginalPath(): void
+    {
+        $tmpDir      = sys_get_temp_dir() . DIRECTORY_SEPARATOR . uniqid('pie_brew_test_', true);
+        $regularFile = $tmpDir . '/regular/pie.phar';
+        $symlinkPath = $tmpDir . '/opt/homebrew/Cellar/pie/1.0/pie';
+
+        mkdir($tmpDir . '/regular', 0777, true);
+        mkdir($tmpDir . '/opt/homebrew/Cellar/pie/1.0', 0777, true);
+        touch($regularFile);
+        symlink($regularFile, $symlinkPath);
+
+        try {
+            $resolvedPath = realpath($symlinkPath);
+            self::assertIsString($resolvedPath);
+            self::assertTrue((new IsBrewInstallation())($resolvedPath, $symlinkPath));
+        } finally {
+            (new Filesystem())->remove($tmpDir);
+        }
+    }
+}