diff --git a/cmd/lk/app.go b/cmd/lk/app.go
index 8a691e2e..8f5cdce1 100644
--- a/cmd/lk/app.go
+++ b/cmd/lk/app.go
@@ -128,6 +128,12 @@ var (
 	}
 )
 
+var missingExecutablePatterns = []*regexp.Regexp{
+	regexp.MustCompile(`(?m)["']?([a-zA-Z0-9][a-zA-Z0-9._+-]*)["']?: executable file not found in (?:\$PATH|%PATH%)`),
+	regexp.MustCompile(`(?m)^(?:env|/usr/bin/env):[ \t]+([a-zA-Z0-9][a-zA-Z0-9._+-]*):[ \t]+No such file or directory[ \t]*\r?$`),
+	regexp.MustCompile(`(?m)^(?:/bin/)?(?:sh|bash|zsh)(?:: [0-9]+)?:[ \t]+([a-zA-Z0-9][a-zA-Z0-9._+-]*):[ \t]+(?:command )?not found[ \t]*\r?$`),
+}
+
 func requireProject(ctx context.Context, cmd *cli.Command) (context.Context, error) {
 	return requireProjectWithOpts(ctx, cmd)
 }
@@ -458,7 +464,7 @@ func setupTemplate(ctx context.Context, cmd *cli.Command) error {
 				b.WriteString(line)
 				b.WriteString("\n")
 			}
-			out.Warnf("%s%sFix your toolchain, then re-run the install step manually in ./%s.", b.String(), fixPrefix, appName)
+			out.Warnf("%s%s%s", b.String(), fixPrefix, installFailureGuidance(err, appName))
 		} else {
 			// Signal a successful install to post_create so the template can skip
 			// printing the now-redundant install hint (guarded via `status:`).
@@ -653,6 +659,30 @@ func doInstall(ctx context.Context, task bootstrap.KnownTask, rootPath string, v
 	return nil
 }
 
+func missingExecutable(message string) string {
+	for _, pattern := range missingExecutablePatterns {
+		matches := pattern.FindStringSubmatch(message)
+		if len(matches) > 1 {
+			return matches[1]
+		}
+	}
+	return ""
+}
+
+func installFailureGuidance(err error, appName string) string {
+	if err != nil {
+		if command := missingExecutable(err.Error()); command != "" {
+			return fmt.Sprintf(
+				"`%s` is required but was not found in PATH. Install `%s`, ensure it is available in PATH, then re-run the install step manually in ./%s.",
+				command,
+				command,
+				appName,
+			)
+		}
+	}
+	return fmt.Sprintf("Fix your toolchain, then re-run the install step manually in ./%s.", appName)
+}
+
 func runTask(ctx context.Context, cmd *cli.Command) error {
 	verbose := cmd.Bool("verbose")
 	rootDir := "."
diff --git a/cmd/lk/app_test.go b/cmd/lk/app_test.go
new file mode 100644
index 00000000..18e05f8a
--- /dev/null
+++ b/cmd/lk/app_test.go
@@ -0,0 +1,95 @@
+// Copyright 2026 LiveKit, Inc.
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package main
+
+import (
+	"errors"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestMissingExecutable(t *testing.T) {
+	tests := []struct {
+		name    string
+		message string
+		want    string
+	}{
+		{
+			name:    "go exec error",
+			message: `"uv": executable file not found in $PATH`,
+			want:    "uv",
+		},
+		{
+			name:    "wrapped go exec error",
+			message: `exec: "pnpm": executable file not found in $PATH`,
+			want:    "pnpm",
+		},
+		{
+			name:    "windows path spelling",
+			message: `exec: "npm": executable file not found in %PATH%`,
+			want:    "npm",
+		},
+		{
+			name:    "env error",
+			message: "env: node: No such file or directory",
+			want:    "node",
+		},
+		{
+			name:    "shell error",
+			message: "sh: yarn: command not found",
+			want:    "yarn",
+		},
+		{
+			name:    "multiline task output",
+			message: "task: [install] uv sync\n\"uv\": executable file not found in $PATH\ntask: Failed to run task \"install\"",
+			want:    "uv",
+		},
+		{
+			name:    "unrelated failure",
+			message: "package installation failed with exit status 1",
+			want:    "",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			assert.Equal(t, tt.want, missingExecutable(tt.message))
+		})
+	}
+}
+
+func TestInstallFailureGuidance(t *testing.T) {
+	t.Run("missing executable", func(t *testing.T) {
+		got := installFailureGuidance(
+			errors.New(`"uv": executable file not found in $PATH`),
+			"my-agent",
+		)
+
+		assert.Equal(t,
+			"`uv` is required but was not found in PATH. Install `uv`, ensure it is available in PATH, then re-run the install step manually in ./my-agent.",
+			got,
+		)
+	})
+
+	t.Run("other install error", func(t *testing.T) {
+		got := installFailureGuidance(errors.New("exit status 1"), "my-agent")
+
+		assert.Equal(t,
+			"Fix your toolchain, then re-run the install step manually in ./my-agent.",
+			got,
+		)
+	})
+}