diff --git a/.github/workflows/test-update-instructions.yml b/.github/workflows/test-update-instructions.yml
new file mode 100644
index 00000000..6802adb1
--- /dev/null
+++ b/.github/workflows/test-update-instructions.yml
@@ -0,0 +1,117 @@
+name: Test Update Instructions
+
+on:
+  pull_request:
+  push:
+
+jobs:
+  unit-tests:
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v3
+      - uses: actions/setup-go@v4
+        with:
+          go-version: "1.24.13"
+      - name: Run unit tests
+        run: go test ./packages/util/ -run TestGetUpdateInstructions -v
+
+  integration-windows:
+    runs-on: windows-latest
+    steps:
+      - uses: actions/checkout@v3
+      - uses: actions/setup-go@v4
+        with:
+          go-version: "1.24.13"
+      - name: Build test helper
+        run: go build -o update-hint.exe ./test/update-hint
+
+      - name: Test scoop path detection
+        shell: pwsh
+        run: |
+          $scoopPath = "$env:USERPROFILE\scoop\apps\infisical\current"
+          New-Item -ItemType Directory -Force -Path $scoopPath | Out-Null
+          Copy-Item update-hint.exe "$scoopPath\update-hint.exe"
+          $output = & "$scoopPath\update-hint.exe"
+          Write-Host "Output: $output"
+          if ($output -notmatch "scoop update infisical") {
+            Write-Error "Expected 'scoop update infisical', got: $output"
+            exit 1
+          }
+
+      - name: Test npm path detection
+        shell: pwsh
+        run: |
+          $npmPath = "$env:APPDATA\npm\node_modules\@infisical\cli\bin"
+          New-Item -ItemType Directory -Force -Path $npmPath | Out-Null
+          Copy-Item update-hint.exe "$npmPath\update-hint.exe"
+          $output = & "$npmPath\update-hint.exe"
+          Write-Host "Output: $output"
+          if ($output -notmatch "npm update -g @infisical/cli") {
+            Write-Error "Expected 'npm update -g @infisical/cli', got: $output"
+            exit 1
+          }
+
+      - name: Test winget path detection
+        shell: pwsh
+        run: |
+          $wingetPath = "$env:LOCALAPPDATA\Microsoft\WinGet\Links"
+          New-Item -ItemType Directory -Force -Path $wingetPath | Out-Null
+          Copy-Item update-hint.exe "$wingetPath\update-hint.exe"
+          $output = & "$wingetPath\update-hint.exe"
+          Write-Host "Output: $output"
+          if ($output -notmatch "winget upgrade Infisical.Infisical") {
+            Write-Error "Expected 'winget upgrade Infisical.Infisical', got: $output"
+            exit 1
+          }
+
+  integration-macos:
+    runs-on: macos-latest
+    steps:
+      - uses: actions/checkout@v3
+      - uses: actions/setup-go@v4
+        with:
+          go-version: "1.24.13"
+      - name: Build test helper
+        run: go build -o update-hint ./test/update-hint
+
+      - name: Test brew path detection
+        run: |
+          mkdir -p /tmp/homebrew/bin
+          cp update-hint /tmp/homebrew/bin/update-hint
+          output=$(/tmp/homebrew/bin/update-hint)
+          echo "Output: $output"
+          echo "$output" | grep -q "brew update" || (echo "Expected brew instruction, got: $output" && exit 1)
+
+      - name: Test npm path detection (via symlink, as npm installs it)
+        run: |
+          mkdir -p /tmp/node_modules/@infisical/cli/bin /tmp/bin
+          cp update-hint /tmp/node_modules/@infisical/cli/bin/update-hint
+          ln -sf /tmp/node_modules/@infisical/cli/bin/update-hint /tmp/bin/update-hint
+          output=$(/tmp/bin/update-hint)
+          echo "Output: $output"
+          echo "$output" | grep -q "npm update -g @infisical/cli" || (echo "Expected npm instruction, got: $output" && exit 1)
+
+  integration-linux:
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v3
+      - uses: actions/setup-go@v4
+        with:
+          go-version: "1.24.13"
+      - name: Build test helper
+        run: go build -o update-hint ./test/update-hint
+
+      - name: Test apt path detection
+        run: |
+          sudo cp update-hint /usr/bin/update-hint
+          output=$(/usr/bin/update-hint)
+          echo "Output: $output"
+          echo "$output" | grep -q "apt-get" || (echo "Expected apt-get instruction, got: $output" && exit 1)
+
+      - name: Test npm path detection
+        run: |
+          mkdir -p $HOME/.npm-global/lib/node_modules/@infisical/cli/bin
+          cp update-hint $HOME/.npm-global/lib/node_modules/@infisical/cli/bin/update-hint
+          output=$($HOME/.npm-global/lib/node_modules/@infisical/cli/bin/update-hint)
+          echo "Output: $output"
+          echo "$output" | grep -q "npm update -g @infisical/cli" || (echo "Expected npm instruction, got: $output" && exit 1)
diff --git a/packages/util/check-for-update.go b/packages/util/check-for-update.go
index 3b7044e9..989841e8 100644
--- a/packages/util/check-for-update.go
+++ b/packages/util/check-for-update.go
@@ -9,6 +9,7 @@ import (
 	"net/http"
 	"os"
 	"os/exec"
+	"path/filepath"
 	"runtime"
 	"strings"
 	"time"
@@ -164,13 +165,41 @@ func getReleasePublishedAt(repoOwner string, repoName string, version string) (t
 }
 
 func GetUpdateInstructions() string {
-	os := runtime.GOOS
-	switch os {
+	execPath, err := os.Executable()
+	if err != nil {
+		execPath = ""
+	}
+	if resolved, err := filepath.EvalSymlinks(execPath); err == nil {
+		execPath = resolved
+	}
+	return getUpdateInstructions(runtime.GOOS, execPath)
+}
+
+func getUpdateInstructions(goos string, execPath string) string {
+	p := strings.ToLower(execPath)
+	isNpm := strings.Contains(p, "node_modules")
+
+	switch goos {
 	case "darwin":
+		if isNpm {
+			return "To update, run: npm update -g @infisical/cli"
+		}
 		return "To update, run: brew update && brew upgrade infisical"
 	case "windows":
+		if isNpm {
+			return "To update, run: npm update -g @infisical/cli"
+		}
+		if strings.Contains(p, "scoop") {
+			return "To update, run: scoop update infisical"
+		}
+		if strings.Contains(p, "winget") {
+			return "To update, run: winget upgrade Infisical.Infisical"
+		}
 		return "To update, run: scoop update infisical"
 	case "linux":
+		if isNpm {
+			return "To update, run: npm update -g @infisical/cli"
+		}
 		pkgManager := getLinuxPackageManager()
 		switch pkgManager {
 		case "apt-get":
diff --git a/packages/util/check-for-update_test.go b/packages/util/check-for-update_test.go
new file mode 100644
index 00000000..802f7004
--- /dev/null
+++ b/packages/util/check-for-update_test.go
@@ -0,0 +1,93 @@
+package util
+
+import (
+	"testing"
+)
+
+func TestGetUpdateInstructions(t *testing.T) {
+	tests := []struct {
+		name     string
+		goos     string
+		execPath string
+		expected string
+	}{
+		// darwin
+		{
+			name:     "darwin brew",
+			goos:     "darwin",
+			execPath: "/opt/homebrew/bin/infisical",
+			expected: "brew update && brew upgrade infisical",
+		},
+		{
+			name:     "darwin npm",
+			goos:     "darwin",
+			execPath: "/opt/homebrew/lib/node_modules/@infisical/cli/bin/infisical",
+			expected: "npm update -g @infisical/cli",
+		},
+
+		// windows
+		{
+			name:     "windows scoop",
+			goos:     "windows",
+			execPath: `C:\Users\user\scoop\apps\infisical\current\infisical.exe`,
+			expected: "scoop update infisical",
+		},
+		{
+			name:     "windows npm",
+			goos:     "windows",
+			execPath: `C:\Users\user\AppData\Roaming\npm\node_modules\@infisical\cli\bin\infisical.exe`,
+			expected: "npm update -g @infisical/cli",
+		},
+		{
+			name:     "windows winget",
+			goos:     "windows",
+			execPath: `C:\Users\user\AppData\Local\Microsoft\WinGet\Links\infisical.exe`,
+			expected: "winget upgrade Infisical.Infisical",
+		},
+		{
+			name:     "windows unknown defaults to scoop",
+			goos:     "windows",
+			execPath: `C:\infisical\infisical.exe`,
+			expected: "scoop update infisical",
+		},
+
+		// linux
+		{
+			name:     "linux apt",
+			goos:     "linux",
+			execPath: "/usr/bin/infisical",
+			expected: "", // apt detection is runtime — tested in integration
+		},
+		{
+			name:     "linux npm",
+			goos:     "linux",
+			execPath: "/home/user/.npm-global/lib/node_modules/@infisical/cli/bin/infisical",
+			expected: "npm update -g @infisical/cli",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result := getUpdateInstructions(tt.goos, tt.execPath)
+			if tt.expected == "" {
+				return // skip runtime-dependent cases
+			}
+			if !contains(result, tt.expected) {
+				t.Errorf("expected %q to contain %q", result, tt.expected)
+			}
+		})
+	}
+}
+
+func contains(s, substr string) bool {
+	return len(s) >= len(substr) && (s == substr || len(s) > 0 && containsStr(s, substr))
+}
+
+func containsStr(s, substr string) bool {
+	for i := 0; i <= len(s)-len(substr); i++ {
+		if s[i:i+len(substr)] == substr {
+			return true
+		}
+	}
+	return false
+}
diff --git a/test/update-hint/main.go b/test/update-hint/main.go
new file mode 100644
index 00000000..eede100a
--- /dev/null
+++ b/test/update-hint/main.go
@@ -0,0 +1,14 @@
+// Helper binary for integration testing of update hint path detection.
+// Prints the update instruction for the current executable path and OS,
+// without making any network calls.
+package main
+
+import (
+	"fmt"
+
+	"github.com/Infisical/infisical-merge/packages/util"
+)
+
+func main() {
+	fmt.Println(util.GetUpdateInstructions())
+}