diff --git a/commands/upgrade.go b/commands/upgrade.go
index e8efb18..a43a82c 100644
--- a/commands/upgrade.go
+++ b/commands/upgrade.go
@@ -2,9 +2,14 @@ package commands
 
 import (
 	"fmt"
+	"os/exec"
+	"path/filepath"
+	"strings"
 
 	"github.com/ci-monk/loli/internal/cli"
 	"github.com/ci-monk/loli/internal/version"
+	"github.com/cli/safeexec"
+	"github.com/kardianos/osext"
 	"github.com/spf13/cobra"
 )
 
@@ -22,10 +27,18 @@ The next time you upgrade, the hidden file will be overwritten.
 You can always delete this file.
 	`,
 	RunE: func(cmd *cobra.Command, args []string) error {
-		c := cli.New(version.GetVersionFormatted())
-		err := updateCLI(c)
-		if err != nil {
-			return fmt.Errorf("we were not able to upgrade the cli because we encountered an error: %s", err)
+		loliBinary, _ := osext.Executable()
+		isHomebrew := isUnderHomebrew(loliBinary)
+
+		if isHomebrew {
+			fmt.Printf("To upgrade, run: %s\n", "brew upgrade gh")
+			return nil
+		} else {
+			c := cli.New(version.GetVersionFormatted())
+			err := updateCLI(c)
+			if err != nil {
+				return fmt.Errorf("we were not able to upgrade the cli because we encountered an error: %s", err)
+			}
 		}
 		return nil
 	},
@@ -45,6 +58,21 @@ func updateCLI(c cli.Updater) error {
 	return c.Upgrade()
 }
 
+func isUnderHomebrew(binary string) bool {
+	brewExe, err := safeexec.LookPath("brew")
+	if err != nil {
+		return false
+	}
+
+	brewPrefixBytes, err := exec.Command(brewExe, "--prefix").Output()
+	if err != nil {
+		return false
+	}
+
+	brewBinPrefix := filepath.Join(strings.TrimSpace(string(brewPrefixBytes)), "bin") + string(filepath.Separator)
+	return strings.HasPrefix(binary, brewBinPrefix)
+}
+
 func init() {
 	rootCmd.AddCommand(upgradeCmd)
 }
diff --git a/go.mod b/go.mod
index 650258c..213c7df 100644
--- a/go.mod
+++ b/go.mod
@@ -6,9 +6,11 @@ require (
 	github.com/blang/semver v3.5.1+incompatible
 	github.com/briandowns/spinner v1.19.0
 	github.com/charmbracelet/glamour v0.5.0
+	github.com/cli/safeexec v1.0.0
 	github.com/fatih/color v1.13.0
 	github.com/inconshreveable/go-update v0.0.0-20160112193335-8152e7eb6ccf
 	github.com/jedib0t/go-pretty v4.3.0+incompatible
+	github.com/kardianos/osext v0.0.0-20190222173326-2bc1f35cddc0
 	github.com/kyokomi/emoji/v2 v2.2.10
 	github.com/logrusorgru/aurora v2.0.3+incompatible
 	github.com/logrusorgru/aurora/v3 v3.0.0
diff --git a/go.sum b/go.sum
index 92e15c5..e235883 100644
--- a/go.sum
+++ b/go.sum
@@ -26,6 +26,8 @@ github.com/briandowns/spinner v1.19.0 h1:s8aq38H+Qju89yhp89b4iIiMzMm8YN3p6vGpwyh
 github.com/briandowns/spinner v1.19.0/go.mod h1:mQak9GHqbspjC/5iUx3qMlIho8xBS/ppAL/hX5SmPJU=
 github.com/charmbracelet/glamour v0.5.0 h1:wu15ykPdB7X6chxugG/NNfDUbyyrCLV9XBalj5wdu3g=
 github.com/charmbracelet/glamour v0.5.0/go.mod h1:9ZRtG19AUIzcTm7FGLGbq3D5WKQ5UyZBbQsMQN0XIqc=
+github.com/cli/safeexec v1.0.0 h1:0VngyaIyqACHdcMNWfo6+KdUYnqEr2Sg+bSP1pdF+dI=
+github.com/cli/safeexec v1.0.0/go.mod h1:Z/D4tTN8Vs5gXYHDCbaM1S/anmEDnJb1iW0+EJ5zx3Q=
 github.com/containerd/console v1.0.3 h1:lIr7SlA5PxZyMV30bDW0MGbiOPXwc63yRuCP0ARubLw=
 github.com/containerd/console v1.0.3/go.mod h1:7LqA/THxQ86k76b8c/EMSiaJ3h1eZkMkXar0TQ1gf3U=
 github.com/cpuguy83/go-md2man/v2 v2.0.2/go.mod h1:tgQtvFlXSQOSOSIRvRPT7W67SCa46tRHOmNcaadrF8o=
@@ -62,6 +64,8 @@ github.com/inconshreveable/mousetrap v1.0.0 h1:Z8tu5sraLXCXIcARxBp/8cbvlwVa7Z1NH
 github.com/inconshreveable/mousetrap v1.0.0/go.mod h1:PxqpIevigyE2G7u3NXJIT2ANytuPF1OarO4DADm73n8=
 github.com/jedib0t/go-pretty v4.3.0+incompatible h1:CGs8AVhEKg/n9YbUenWmNStRW2PHJzaeDodcfvRAbIo=
 github.com/jedib0t/go-pretty v4.3.0+incompatible/go.mod h1:XemHduiw8R651AF9Pt4FwCTKeG3oo7hrHJAoznj9nag=
+github.com/kardianos/osext v0.0.0-20190222173326-2bc1f35cddc0 h1:iQTw/8FWTuc7uiaSepXwyf3o52HaUYcV+Tu66S3F5GA=
+github.com/kardianos/osext v0.0.0-20190222173326-2bc1f35cddc0/go.mod h1:1NbS8ALrpOvjt0rHPNLyCIeMtbizbir8U//inJ+zuB8=
 github.com/klauspost/compress v1.13.6/go.mod h1:/3/Vjq9QcHkK5uEr5lBEmyoZ1iFhe47etQ6QUkpK6sk=
 github.com/klauspost/cpuid/v2 v2.0.9/go.mod h1:FInQzS24/EEf25PyTYn52gqo7WaD8xa0213Md/qVLRg=
 github.com/klauspost/cpuid/v2 v2.0.10/go.mod h1:g2LTdtYhdyuGPqyWyv7qRAmj1WBqxuObKfj5c0PQa7c=