diff --git a/.github/workflows/pr-ci.yml b/.github/workflows/pr-ci.yml
index 7cf8dab6a..a3069ab21 100644
--- a/.github/workflows/pr-ci.yml
+++ b/.github/workflows/pr-ci.yml
@@ -135,6 +135,7 @@ jobs:
           name: e2e-test-${{ steps.os.outputs.runner_os }}
           path: ./e2e/e2e.test*
 
+
   licenses:
     name: Third-party licenses
     needs: [changes, precommit, lint]
@@ -578,6 +579,12 @@ jobs:
             free-disk-space: false
             install-kind: true
             requires-secret: false
+          - label: ssh-proxy-command
+            runner: windows-latest
+            free-disk-space: false
+            install-kind: true
+            requires-secret: false
+
 
     runs-on: ${{ matrix.runner }}
     timeout-minutes: ${{ matrix.job-timeout-minutes || 45 }}
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 55368d5b3..c4cf565dc 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -62,8 +62,10 @@ repos:
     rev: v2.12.2
     hooks:
       - id: golangci-lint
+        language_version: 1.26.5
         args: ["--timeout=10m"]
       - id: golangci-lint-fmt
+        language_version: 1.26.5
   - repo: local
     hooks:
       - id: golangci-lint-ci-parity
diff --git a/e2e/tests/ssh/proxy_command.go b/e2e/tests/ssh/proxy_command.go
new file mode 100644
index 000000000..88e4aa353
--- /dev/null
+++ b/e2e/tests/ssh/proxy_command.go
@@ -0,0 +1,109 @@
+package ssh
+
+import (
+	"bytes"
+	"context"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"runtime"
+	"strings"
+	"time"
+
+	"github.com/devsy-org/devsy/e2e/framework"
+	"github.com/onsi/ginkgo/v2"
+	"github.com/onsi/gomega"
+)
+
+var _ = ginkgo.Describe(
+	"devsy Windows SSH ProxyCommand",
+	ginkgo.Label("ssh-proxy-command"),
+	func() {
+		var initialDir string
+
+		ginkgo.BeforeEach(func() {
+			var err error
+			initialDir, err = os.Getwd()
+			framework.ExpectNoError(err)
+		})
+
+		ginkgo.It(
+			"should launch a workspace through an executable path containing spaces",
+			ginkgo.SpecTimeout(framework.TimeoutLong()),
+			func(ctx context.Context) {
+				if runtime.GOOS != osWindows {
+					ginkgo.Skip("skipping on non-Windows")
+				}
+
+				tempDir, err := framework.CopyToTempDir("tests/ssh/testdata/local-test")
+				framework.ExpectNoError(err)
+
+				baseFramework := framework.NewDefaultFramework(initialDir + "/bin")
+				sourcePath := filepath.Join(baseFramework.DevsyBinDir, baseFramework.DevsyBinName)
+				fixtureDir := filepath.Join(ginkgo.GinkgoT().TempDir(), "Devsy Test")
+				framework.ExpectNoError(os.MkdirAll(fixtureDir, 0o700))
+				fixturePath := filepath.Join(fixtureDir, baseFramework.DevsyBinName)
+				// #nosec G304 -- controlled path to the E2E fixture binary
+				binary, err := os.ReadFile(sourcePath)
+				framework.ExpectNoError(err)
+				framework.ExpectNoError(os.WriteFile(fixturePath, binary, 0o600))
+				gomega.Expect(fixturePath).To(gomega.ContainSubstring(" "))
+
+				f, err := framework.SetupDockerProvider(fixtureDir, "podman")
+				framework.ExpectNoError(err)
+
+				sshConfigPath := filepath.Join(ginkgo.GinkgoT().TempDir(), "ssh config")
+				ginkgo.DeferCleanup(func(cleanupCtx context.Context) {
+					_ = f.DevsyWorkspaceDelete(cleanupCtx, tempDir)
+					framework.CleanupTempDir(initialDir, tempDir)
+				})
+
+				upCtx, cancelUp := context.WithTimeout(ctx, 5*time.Minute)
+				defer cancelUp()
+				err = f.DevsyUp(upCtx, tempDir, "--ssh-config", sshConfigPath)
+				framework.ExpectNoError(err)
+
+				configBytes, err := os.ReadFile(filepath.Clean(sshConfigPath))
+				framework.ExpectNoError(err)
+				config := string(configBytes)
+				expectedPath := strings.ReplaceAll(fixturePath, `\`, "/")
+				gomega.Expect(config).To(
+					gomega.ContainSubstring(`ProxyCommand "`+expectedPath+`"`),
+					"SSH config should use forward slashes for the executable path",
+				)
+				gomega.Expect(config).NotTo(
+					gomega.ContainSubstring(fixturePath),
+					"SSH config should not contain the native Windows executable path",
+				)
+
+				sshPath, err := exec.LookPath("ssh.exe")
+				framework.ExpectNoError(err)
+				host := filepath.Base(tempDir) + ".devsy"
+				sshCtx, cancelSSH := context.WithTimeout(ctx, 30*time.Second)
+				defer cancelSSH()
+				// #nosec G204 -- controlled OpenSSH invocation for the E2E test
+				cmd := exec.CommandContext(
+					sshCtx,
+					sshPath,
+					"-F", sshConfigPath,
+					"-o", "BatchMode=yes",
+					host,
+					"printf",
+					"proxy-command-ok",
+				)
+				var stdout, stderr bytes.Buffer
+				cmd.Stdout = &stdout
+				cmd.Stderr = &stderr
+				err = cmd.Run()
+				framework.ExpectNoError(
+					err,
+					"OpenSSH should launch ProxyCommand; stdout=%q stderr=%q",
+					stdout.String(), stderr.String(),
+				)
+				gomega.Expect(strings.TrimSpace(stdout.String())).To(
+					gomega.Equal("proxy-command-ok"),
+				)
+			},
+		)
+	},
+)
diff --git a/pkg/ssh/config.go b/pkg/ssh/config.go
index 2b55d9300..9c354bea1 100644
--- a/pkg/ssh/config.go
+++ b/pkg/ssh/config.go
@@ -25,6 +25,8 @@ var (
 	MarkerEndPrefix   = "# Devsy End "
 )
 
+const windowsGOOS = "windows"
+
 type SSHConfigParams struct {
 	SSHConfigPath        string
 	SSHConfigIncludePath string
@@ -112,11 +114,32 @@ type proxyCommandBuilder struct {
 	options     []string
 }
 
+func normalizeSSHExecPath(execPath string) string {
+	return normalizeSSHExecPathForOS(execPath, runtime.GOOS)
+}
+
+func normalizeSSHExecPathForOS(execPath, goos string) string {
+	if goos == windowsGOOS {
+		return strings.ReplaceAll(execPath, `\`, "/")
+	}
+
+	return execPath
+}
+
 func newProxyCommandBuilder(execPath, context, user, workspace string) *proxyCommandBuilder {
+	normalizedExecPath := normalizeSSHExecPath(execPath)
+	log.Debugw(
+		"ssh proxy command config",
+		"os", runtime.GOOS,
+		"executable_raw", execPath,
+		"executable_normalized", normalizedExecPath,
+		"workspace", workspace,
+	)
+
 	return &proxyCommandBuilder{
 		baseCommand: fmt.Sprintf(
 			"\"%s\" workspace ssh %s %s %s %s %s %s",
-			execPath,
+			normalizedExecPath,
 			names.Flag(names.Stdio),
 			names.Flag(names.Context),
 			context,
@@ -296,7 +319,7 @@ func mergeSSHConfig(lines, newLines []string, position int) string {
 	merged := slices.Insert(lines, position, newLines...)
 
 	newLineSep := "\n"
-	if runtime.GOOS == "windows" {
+	if runtime.GOOS == windowsGOOS {
 		newLineSep = "\r\n"
 	}
 
diff --git a/pkg/ssh/config_test.go b/pkg/ssh/config_test.go
index 4af4b5778..a6ddcb5a6 100644
--- a/pkg/ssh/config_test.go
+++ b/pkg/ssh/config_test.go
@@ -369,3 +369,43 @@ func (s *SSHConfigTestSuite) TestAddHostSection() {
 		})
 	}
 }
+
+func TestNormalizeSSHExecPathForOS(t *testing.T) {
+	tests := []struct {
+		name     string
+		goos     string
+		input    string
+		expected string
+	}{
+		{
+			name:     "windows path",
+			goos:     windowsGOOS,
+			input:    `C:\Users\test\AppData\Local\Programs\Devsy\devsy.exe`,
+			expected: `C:/Users/test/AppData/Local/Programs/Devsy/devsy.exe`,
+		},
+		{
+			name:     "windows path with spaces",
+			goos:     windowsGOOS,
+			input:    `C:\Users\Test User\AppData\Local\Programs\Devsy\devsy.exe`,
+			expected: `C:/Users/Test User/AppData/Local/Programs/Devsy/devsy.exe`,
+		},
+		{
+			name:     "linux path",
+			goos:     "linux",
+			input:    `/usr/local/bin/devsy`,
+			expected: `/usr/local/bin/devsy`,
+		},
+		{
+			name:     "macos path",
+			goos:     "darwin",
+			input:    `/Applications/Devsy.app/Contents/MacOS/devsy`,
+			expected: `/Applications/Devsy.app/Contents/MacOS/devsy`,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			assert.Equal(t, tt.expected, normalizeSSHExecPathForOS(tt.input, tt.goos))
+		})
+	}
+}
diff --git a/pkg/ssh/config_windows_test.go b/pkg/ssh/config_windows_test.go
new file mode 100644
index 000000000..4f2d4a99a
--- /dev/null
+++ b/pkg/ssh/config_windows_test.go
@@ -0,0 +1,28 @@
+//go:build windows
+
+package ssh
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestAddHostSectionNormalizesWindowsExecPath(t *testing.T) {
+	execPath := `C:\Users\Test User\AppData\Local\Programs\Devsy\resources\bin\devsy.exe`
+	result, err := addHostSection("", execPath, addHostParams{
+		host:      "testhost",
+		user:      "ubuntu",
+		context:   "default",
+		workspace: "testworkspace",
+		workdir:   "/workspaces/project",
+	})
+	require.NoError(t, err)
+	require.Contains(
+		t,
+		result,
+		`ProxyCommand "C:/Users/Test User/AppData/Local/Programs/Devsy/resources/bin/devsy.exe" workspace ssh --stdio --context default --user ubuntu testworkspace`,
+	)
+	require.NotContains(t, result, `C:\Users\Test User`)
+	require.Contains(t, result, `--workdir "/workspaces/project"`)
+}
diff --git a/renovate.json b/renovate.json
index 621488003..475b16ff3 100644
--- a/renovate.json
+++ b/renovate.json
@@ -33,6 +33,15 @@
       "automerge": true,
       "prPriority": 4
     },
+    {
+      "matchManagers": ["pre-commit"],
+      "matchPackageNames": ["https://github.com/golangci/golangci-lint"],
+      "matchFileNames": [".pre-commit-config.yaml"],
+      "allowedVersions": "v2.12.2",
+      "automerge": false,
+      "description": "keep golangci-lint aligned with the pinned Go 1.26.5 toolchain"
+    },
+
     {
       "matchManagers": ["gomod"],
       "automerge": true,