feat: enforce proxy dial timeouts and improve timeout handling

easyssh.go

@@ -28,6 +28,11 @@ var (
 	defaultBufferSize = 4096
 )
 
+var (
+	// ErrProxyDialTimeout is returned when proxy dial connection times out
+	ErrProxyDialTimeout = errors.New("proxy dial timeout")
+)
+
 type Protocol string
 
 const (
@@ -253,7 +258,35 @@ func (ssh_conf *MakeConfig) Connect() (*ssh.Session, *ssh.Client, error) {
 			return nil, nil, err
 		}
 
-		conn, err := proxyClient.Dial(string(ssh_conf.Protocol), net.JoinHostPort(ssh_conf.Server, ssh_conf.Port))
+		// Apply timeout to the connection from proxy to target server
+		timeout := ssh_conf.Timeout
+		if timeout == 0 {
+			timeout = defaultTimeout
+		}
+
+		ctx, cancel := context.WithTimeout(context.Background(), timeout)
+		defer cancel()
+
+		type connResult struct {
+			conn net.Conn
+			err  error
+		}
+
+		connCh := make(chan connResult, 1)
+		go func() {
+			conn, err := proxyClient.Dial(string(ssh_conf.Protocol), net.JoinHostPort(ssh_conf.Server, ssh_conf.Port))
+			connCh <- connResult{conn: conn, err: err}
+		}()
+
+		var conn net.Conn
+		select {
+		case result := <-connCh:
+			conn = result.conn
+			err = result.err
+		case <-ctx.Done():
+			return nil, nil, fmt.Errorf("%w: %v", ErrProxyDialTimeout, ctx.Err())
+		}
+
 		if err != nil {
 			return nil, nil, err
 		}
@@ -413,6 +446,10 @@ func (ssh_conf *MakeConfig) Stream(command string, timeout ...time.Duration) (<-
 func (ssh_conf *MakeConfig) Run(command string, timeout ...time.Duration) (outStr string, errStr string, isTimeout bool, err error) {
 	stdoutChan, stderrChan, doneChan, errChan, err := ssh_conf.Stream(command, timeout...)
 	if err != nil {
+		// Check if the error is from a proxy dial timeout
+		if errors.Is(err, ErrProxyDialTimeout) {
+			isTimeout = true
+		}
 		return outStr, errStr, isTimeout, err
 	}
 	// read from the output channel until the done signal is passed

easyssh_test.go

@@ -2,6 +2,7 @@ package easyssh
 
 import (
 	"context"
+	"errors"
 	"os"
 	"os/user"
 	"path"
@@ -512,3 +513,117 @@ func TestCommandTimeout(t *testing.T) {
 	assert.NotNil(t, err)
 	assert.Equal(t, "Run Command Timeout: "+context.DeadlineExceeded.Error(), err.Error())
 }
+
+// TestProxyTimeoutHandling tests that timeout is properly respected when using proxy connections
+// This test uses a non-existent proxy server to force a timeout during proxy connection
+func TestProxyTimeoutHandling(t *testing.T) {
+	ssh := &MakeConfig{
+		Server:  "example.com",
+		User:    "testuser",
+		Port:    "22",
+		KeyPath: "./tests/.ssh/id_rsa",
+		Timeout: 1 * time.Second, // Short timeout for testing
+		Proxy: DefaultConfig{
+			User:    "testuser",
+			Server:  "10.255.255.1", // Non-routable IP that should timeout
+			Port:    "22",
+			KeyPath: "./tests/.ssh/id_rsa",
+			Timeout: 1 * time.Second,
+		},
+	}
+
+	// Test Connect() method directly to test proxy connection timeout
+	start := time.Now()
+	session, client, err := ssh.Connect()
+	elapsed := time.Since(start)
+
+	// Should timeout within reasonable bounds
+	assert.True(t, elapsed < 3*time.Second, "Connection should timeout within 3 seconds, took %v", elapsed)
+	assert.True(t, elapsed >= 1*time.Second, "Connection should take at least 1 second (timeout value), took %v", elapsed)
+
+	// Should return nil session and client
+	assert.Nil(t, session)
+	assert.Nil(t, client)
+
+	// Should have error
+	assert.NotNil(t, err)
+}
+
+// TestProxyDialTimeout tests the specific scenario described in issue #93
+// where proxy dial timeout should be respected and properly detected
+func TestProxyDialTimeout(t *testing.T) {
+	ssh := &MakeConfig{
+		Server:  "10.255.255.1", // Non-routable IP that should timeout
+		User:    "testuser",
+		Port:    "22",
+		KeyPath: "./tests/.ssh/id_rsa",
+		Timeout: 2 * time.Second, // Short timeout for testing
+		Proxy: DefaultConfig{
+			User:    "testuser",
+			Server:  "10.255.255.2", // Another non-routable IP for proxy
+			Port:    "22",
+			KeyPath: "./tests/.ssh/id_rsa",
+			Timeout: 2 * time.Second,
+		},
+	}
+
+	// Test Connect() method directly to avoid SSH server dependency
+	start := time.Now()
+	session, client, err := ssh.Connect()
+	elapsed := time.Since(start)
+
+	// Should timeout within reasonable bounds
+	assert.True(t, elapsed < 5*time.Second, "Connection should timeout within 5 seconds, took %v", elapsed)
+	assert.True(t, elapsed >= 2*time.Second, "Connection should take at least 2 seconds (timeout value), took %v", elapsed)
+
+	// Should return nil session and client
+	assert.Nil(t, session)
+	assert.Nil(t, client)
+
+	// Should have error
+	assert.NotNil(t, err)
+	// Note: This will timeout at the proxy connection level, not at proxy dial level
+	// so it won't be ErrProxyDialTimeout, but we can still verify the timeout behavior
+}
+
+// TestProxyDialTimeoutInRun tests timeout detection in Run method
+func TestProxyDialTimeoutInRun(t *testing.T) {
+	ssh := &MakeConfig{
+		Server:  "example.com",
+		User:    "testuser",
+		Port:    "22",
+		KeyPath: "./tests/.ssh/id_rsa",
+		Timeout: 2 * time.Second,
+		Proxy: DefaultConfig{
+			User:    "testuser",
+			Server:  "127.0.0.1", // Assume localhost SSH exists
+			Port:    "22",
+			KeyPath: "./tests/.ssh/id_rsa",
+			Timeout: 2 * time.Second,
+		},
+	}
+
+	// Mock a scenario where Connect() returns ErrProxyDialTimeout
+	// by temporarily changing the target to a non-routable address
+	ssh.Server = "10.255.255.1"
+
+	start := time.Now()
+	outStr, errStr, isTimeout, err := ssh.Run("whoami")
+	elapsed := time.Since(start)
+
+	// Should timeout within reasonable bounds
+	assert.True(t, elapsed < 5*time.Second, "Should timeout within 5 seconds, took %v", elapsed)
+
+	// Should return empty output
+	assert.Equal(t, "", outStr)
+	assert.Equal(t, "", errStr)
+
+	// Should have error
+	assert.NotNil(t, err)
+
+	// If it's specifically a proxy dial timeout, isTimeout should be true
+	if errors.Is(err, ErrProxyDialTimeout) {
+		assert.True(t, isTimeout, "isTimeout should be true for proxy dial timeout")
+	}
+}
+