diff --git a/cli/ssh.go b/cli/ssh.go
index d18ac8909f575..bf1299ea944ad 100644
--- a/cli/ssh.go
+++ b/cli/ssh.go
@@ -18,6 +18,7 @@ import (
 	"slices"
 	"strings"
 	"sync"
+	"sync/atomic"
 	"time"
 
 	"github.com/gen2brain/beeep"
@@ -247,9 +248,28 @@ func (r *RootCmd) ssh() *serpent.Command {
 			// In stdio mode, we can't allow any writes to stdin or stdout
 			// because they are used by the SSH protocol.
 			stdioReader, stdioWriter := inv.Stdin, inv.Stdout
+			// connected is set once the SSH session is consuming stdin, at
+			// which point its copy logic handles stdin termination.
+			var connected atomic.Bool
 			if stdio {
 				inv.Stdin = stdioErrLogReader{inv.Logger}
 				inv.Stdout = inv.Stderr
+
+				// ProxyCommand clients close stdin when they abandon a
+				// connection attempt. Relay stdin through a pipe so that its
+				// termination is observed even before the connection exists,
+				// canceling this process instead of leaking it while it waits
+				// for the agent or dials. See #27954.
+				piper, pipew := io.Pipe()
+				go func(src io.Reader) {
+					_, err := io.Copy(pipew, src)
+					_ = pipew.CloseWithError(err)
+					logger.Debug(ctx, "stdin relay finished", slog.Error(err))
+					if !connected.Load() {
+						cancel()
+					}
+				}(stdioReader)
+				stdioReader = piper
 			}
 
 			// This WaitGroup solves for a race condition where we were logging
@@ -460,6 +480,7 @@ func (r *RootCmd) ssh() *serpent.Command {
 						})
 						defer closeUsage()
 					}
+					connected.Store(true)
 					return runCoderConnectStdio(ctx, fmt.Sprintf("%s:22", coderConnectHost), stdioReader, stdioWriter, stack, logger)
 				}
 			}
@@ -549,6 +570,7 @@ func (r *RootCmd) ssh() *serpent.Command {
 						return nil
 					}, logger, client, workspace, errCh)
 				}()
+				connected.Store(true)
 				copier.copy(&wg)
 				return nil
 			}
diff --git a/cli/ssh_test.go b/cli/ssh_test.go
index 2221a23e7bf9c..c90cc6a0a81a4 100644
--- a/cli/ssh_test.go
+++ b/cli/ssh_test.go
@@ -2170,8 +2170,17 @@ func TestSSH_CoderConnect(t *testing.T) {
 		ctx = context.WithValue(ctx, "fs", fs)
 
 		client, workspace, agentToken := setupWorkspaceForAgent(t)
+		// Provide a live stdin for the command; with no stdin attached, the
+		// command treats it as an abandoned connection and exits early.
+		clientOutput, clientInput := io.Pipe()
+		defer func() {
+			for _, c := range []io.Closer{clientOutput, clientInput} {
+				_ = c.Close()
+			}
+		}()
 		inv, root := clitest.New(t, "ssh", workspace.Name, "--network-info-dir", "/net", "--stdio")
 		clitest.SetupConfig(t, client, root)
+		inv.Stdin = clientOutput
 
 		ctx = cli.WithTestOnlyCoderConnectDialer(ctx, &fakeCoderConnectDialer{})
 		ctx = withCoderConnectRunning(ctx)
@@ -2457,6 +2466,48 @@ func (*fakeCoderConnectDialer) DialContext(ctx context.Context, network, addr st
 	return nil, xerrors.Errorf("dial coder connect host %q over %s", addr, network)
 }
 
+// TestSSHStdio_ExitWhenStdinClosedBeforeAgentConnects ensures the command exits
+// promptly when the client closes stdin before a connection is established,
+// instead of leaking the process while waiting for the agent or dialing.
+// See https://github.com/coder/coder/issues/27954
+func TestSSHStdio_ExitWhenStdinClosedBeforeAgentConnects(t *testing.T) {
+	t.Parallel()
+
+	client, workspace, _ := setupWorkspaceForAgent(t)
+
+	clientOutput, clientInput := io.Pipe()
+	serverOutput, serverInput := io.Pipe()
+	defer func() {
+		for _, c := range []io.Closer{clientOutput, clientInput, serverOutput, serverInput} {
+			_ = c.Close()
+		}
+	}()
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitMedium)
+	defer cancel()
+
+	inv, root := clitest.New(t, "ssh", "--stdio", workspace.Name)
+	clitest.SetupConfig(t, client, root)
+	inv.Stdin = clientOutput
+	inv.Stdout = serverInput
+	inv.Stderr = io.Discard
+
+	cmdDone := tGo(t, func() {
+		err := inv.WithContext(ctx).Run()
+		assert.Error(t, err)
+	})
+
+	// The client abandons the connection attempt by closing stdin. No agent
+	// is started, so the command would wait for it forever unless it notices.
+	require.NoError(t, clientOutput.Close())
+
+	select {
+	case <-cmdDone:
+	case <-time.After(testutil.WaitShort):
+		require.Fail(t, "coder ssh --stdio did not exit after stdin was closed")
+	}
+}
+
 // tGoContext runs fn in a goroutine passing a context that will be
 // canceled on test completion and wait until fn has finished executing.
 // Done and cancel are returned for optionally waiting until completion