diff --git a/Dockerfile b/Dockerfile
index ffd6b8e..9420c3b 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,7 +1,7 @@
 # NB: this image isn't used anywhere in the build pipeline. It exists to
 # conveniently facilitate ad-hoc experimentation in a sandboxed environment
 # during development.
-FROM golang:1.15-alpine
+FROM golang:1.26-alpine
 
 RUN apk add git less make
 
diff --git a/cmd/cheat/first_run_integration_test.go b/cmd/cheat/first_run_integration_test.go
new file mode 100644
index 0000000..6a699bb
--- /dev/null
+++ b/cmd/cheat/first_run_integration_test.go
@@ -0,0 +1,180 @@
+package main
+
+import (
+	"os"
+	"os/exec"
+	"path/filepath"
+	"runtime"
+	"strings"
+	"testing"
+)
+
+// TestFirstRunIntegration exercises the end-to-end first-run experience:
+// no config exists, the binary creates one, and subsequent runs succeed.
+// This is the regression test for issues #721, #771, and #730.
+func TestFirstRunIntegration(t *testing.T) {
+	// Build the cheat binary
+	binName := "cheat_test"
+	if runtime.GOOS == "windows" {
+		binName += ".exe"
+	}
+	binPath := filepath.Join(t.TempDir(), binName)
+	build := exec.Command("go", "build", "-o", binPath, ".")
+	if output, err := build.CombinedOutput(); err != nil {
+		t.Fatalf("failed to build cheat: %v\nOutput: %s", err, output)
+	}
+
+	t.Run("decline config creation", func(t *testing.T) {
+		testHome := t.TempDir()
+		env := firstRunEnv(testHome)
+
+		cmd := exec.Command(binPath)
+		cmd.Env = env
+		cmd.Stdin = strings.NewReader("n\n")
+		output, err := cmd.CombinedOutput()
+		if err != nil {
+			t.Fatalf("cheat exited with error: %v\nOutput: %s", err, output)
+		}
+
+		// Verify no config was created
+		if firstRunConfigExists(testHome) {
+			t.Error("config file was created despite user declining")
+		}
+	})
+
+	t.Run("accept config decline community", func(t *testing.T) {
+		testHome := t.TempDir()
+		env := firstRunEnv(testHome)
+
+		// First run: yes to create config, no to community cheatsheets
+		cmd := exec.Command(binPath)
+		cmd.Env = env
+		cmd.Stdin = strings.NewReader("y\nn\n")
+		output, err := cmd.CombinedOutput()
+		if err != nil {
+			t.Fatalf("first run failed: %v\nOutput: %s", err, output)
+		}
+		outStr := string(output)
+
+		// Parse the config path from output
+		confpath := parseCreatedConfPath(t, outStr)
+		if confpath == "" {
+			t.Fatalf("could not find config path in output:\n%s", outStr)
+		}
+
+		// Verify config file exists
+		if _, err := os.Stat(confpath); os.IsNotExist(err) {
+			t.Fatalf("config file not found at %s", confpath)
+		}
+
+		// Verify community cheatpath is commented out in config
+		content, err := os.ReadFile(confpath)
+		if err != nil {
+			t.Fatalf("failed to read config: %v", err)
+		}
+		contentStr := string(content)
+		for _, line := range strings.Split(contentStr, "\n") {
+			trimmed := strings.TrimSpace(line)
+			if trimmed == "- name: community" {
+				t.Error("community cheatpath should be commented out")
+				break
+			}
+		}
+
+		// Verify personal and work directories were created
+		confdir := filepath.Dir(confpath)
+		for _, name := range []string{"personal", "work"} {
+			dir := filepath.Join(confdir, "cheatsheets", name)
+			if _, err := os.Stat(dir); os.IsNotExist(err) {
+				t.Errorf("expected %s directory at %s", name, dir)
+			}
+		}
+
+		// Community directory should NOT exist
+		communityDir := filepath.Join(confdir, "cheatsheets", "community")
+		if _, err := os.Stat(communityDir); err == nil {
+			t.Error("community directory should not exist when declined")
+		}
+
+		// --- Second run: verify the config loads successfully ---
+		// This is the core regression test for #721/#771/#730:
+		// previously, the second run would fail because config.New()
+		// hard-errored on the missing community cheatpath directory.
+		// Use --directories (not --list, which exits 2 when no sheets exist).
+		cmd2 := exec.Command(binPath, "--directories")
+		cmd2.Env = append(append([]string{}, env...), "CHEAT_CONFIG_PATH="+confpath)
+		output2, err := cmd2.CombinedOutput()
+		if err != nil {
+			t.Fatalf(
+				"second run failed (regression for #721/#771/#730): %v\nOutput: %s",
+				err, output2,
+			)
+		}
+
+		// Verify the output lists the expected cheatpaths
+		outStr2 := string(output2)
+		if !strings.Contains(outStr2, "personal") {
+			t.Errorf("expected 'personal' cheatpath in --directories output:\n%s", outStr2)
+		}
+		if !strings.Contains(outStr2, "work") {
+			t.Errorf("expected 'work' cheatpath in --directories output:\n%s", outStr2)
+		}
+	})
+}
+
+// firstRunEnv returns a minimal environment for a clean first-run test.
+func firstRunEnv(home string) []string {
+	env := []string{
+		"PATH=" + os.Getenv("PATH"),
+	}
+
+	switch runtime.GOOS {
+	case "windows":
+		env = append(env,
+			"APPDATA="+filepath.Join(home, "AppData", "Roaming"),
+			"USERPROFILE="+home,
+			"SystemRoot="+os.Getenv("SystemRoot"),
+		)
+	default:
+		env = append(env,
+			"HOME="+home,
+			"EDITOR=vi",
+		)
+	}
+
+	return env
+}
+
+// parseCreatedConfPath extracts the config file path from the installer's
+// "Created config file: <path>" output. The message may appear mid-line
+// (after prompt text), so we search for the substring anywhere in the output.
+func parseCreatedConfPath(t *testing.T, output string) string {
+	t.Helper()
+	const marker = "Created config file: "
+	idx := strings.Index(output, marker)
+	if idx < 0 {
+		return ""
+	}
+	rest := output[idx+len(marker):]
+	// the path ends at the next newline
+	if nl := strings.IndexByte(rest, '\n'); nl >= 0 {
+		rest = rest[:nl]
+	}
+	return strings.TrimSpace(rest)
+}
+
+// firstRunConfigExists checks whether a cheat config file exists under the
+// given home directory at any of the standard locations.
+func firstRunConfigExists(home string) bool {
+	candidates := []string{
+		filepath.Join(home, ".config", "cheat", "conf.yml"),
+		filepath.Join(home, ".cheat", "conf.yml"),
+		filepath.Join(home, "AppData", "Roaming", "cheat", "conf.yml"),
+	}
+	for _, p := range candidates {
+		if _, err := os.Stat(p); err == nil {
+			return true
+		}
+	}
+	return false
+}
diff --git a/internal/installer/prompt.go b/internal/installer/prompt.go
index 3807dde..3c97241 100644
--- a/internal/installer/prompt.go
+++ b/internal/installer/prompt.go
@@ -3,7 +3,6 @@
 package installer
 
 import (
-	"bufio"
 	"fmt"
 	"os"
 	"strings"
@@ -12,20 +11,34 @@ import (
 // Prompt prompts the user for a answer
 func Prompt(prompt string, def bool) (bool, error) {
 
-	// initialize a line reader
-	reader := bufio.NewReader(os.Stdin)
-
 	// display the prompt
 	fmt.Printf("%s: ", prompt)
 
-	// read the answer
-	ans, err := reader.ReadString('\n')
-	if err != nil {
-		return false, fmt.Errorf("failed to parse input: %v", err)
+	// read one byte at a time until newline to avoid buffering past the
+	// end of the current line, which would consume input intended for
+	// subsequent Prompt calls on the same stdin
+	var line []byte
+	buf := make([]byte, 1)
+	for {
+		n, err := os.Stdin.Read(buf)
+		if n > 0 {
+			if buf[0] == '\n' {
+				break
+			}
+			if buf[0] != '\r' {
+				line = append(line, buf[0])
+			}
+		}
+		if err != nil {
+			if len(line) > 0 {
+				break
+			}
+			return false, fmt.Errorf("failed to prompt: %v", err)
+		}
 	}
 
 	// normalize the answer
-	ans = strings.ToLower(strings.TrimSpace(ans))
+	ans := strings.ToLower(strings.TrimSpace(string(line)))
 
 	// return the appropriate response
 	switch ans {
diff --git a/internal/installer/prompt_test.go b/internal/installer/prompt_test.go
index 8b8fe19..faf28b6 100644
--- a/internal/installer/prompt_test.go
+++ b/internal/installer/prompt_test.go
@@ -154,8 +154,8 @@ func TestPromptError(t *testing.T) {
 	if err == nil {
 		t.Error("expected error when reading from closed stdin, got nil")
 	}
-	if !strings.Contains(err.Error(), "failed to parse input") {
-		t.Errorf("expected 'failed to parse input' error, got: %v", err)
+	if !strings.Contains(err.Error(), "failed to prompt") {
+		t.Errorf("expected 'failed to prompt' error, got: %v", err)
 	}
 }