wolfSSL · yosuke-wolfssl · Jun 15, 2026
diff --git a/.github/workflows/windows-check.yml b/.github/workflows/windows-check.yml
@@ -43,13 +43,12 @@ jobs:
       working-directory: ${{env.GITHUB_WORKSPACE}}wolfssl
       run: nuget restore ${{env.WOLFSSL_SOLUTION_FILE_PATH}}
 
-    - name: updated user_settings.h for sshd and x509
+    - name: Enable wolfSSH options (sshd, sftp, x509) in user_settings.h
       working-directory: ${{env.GITHUB_WORKSPACE}}
-      run: cp ${{env.USER_SETTINGS_H_NEW}} ${{env.USER_SETTINGS_H}}
-
-    - name: replace wolfSSL user_settings.h with wolfSSH user_settings.h
-      working-directory: ${{env.GITHUB_WORKSPACE}}
-      run: get-content ${{env.USER_SETTINGS_H_NEW}} | %{$_ -replace "if 0","if 1"}
+      shell: bash
+      run: |
+        sed -i 's/#if 0/#if 1/g' ${{env.USER_SETTINGS_H_NEW}}
+        cp ${{env.USER_SETTINGS_H_NEW}} ${{env.USER_SETTINGS_H}}
 
     - name: Build wolfssl library
       working-directory: ${{env.GITHUB_WORKSPACE}}wolfssl
@@ -65,3 +64,27 @@ jobs:
       # See https://docs.microsoft.com/visualstudio/msbuild/msbuild-command-line-reference
       run: msbuild /m /p:PlatformToolset=v142 /p:Platform=${{env.BUILD_PLATFORM}} /p:WindowsTargetPlatformVersion=${{env.TARGET_PLATFORM}} /p:Configuration=${{env.WOLFSSH_BUILD_CONFIGURATION}} ${{env.SOLUTION_FILE_PATH}}
 
+    - name: Locate wolfsshd.exe and stage wolfssl.dll
+      working-directory: ${{ github.workspace }}\wolfssh
+      shell: pwsh
+      run: |
+        $sshdExe = Get-ChildItem -Path "${{ github.workspace }}\wolfssh" -Recurse -Filter "wolfsshd.exe" -ErrorAction SilentlyContinue |
+            Where-Object { $_.FullName -like "*Release*" } | Select-Object -First 1
+        if (-not $sshdExe) {
+            Write-Host "ERROR: wolfsshd.exe not found"
+            exit 1
+        }
+        Add-Content -Path $env:GITHUB_ENV -Value "SSHD_PATH=$($sshdExe.FullName)"
+
+        $sshdDir = Split-Path -Parent $sshdExe.FullName
+        $wolfsslDll = Get-ChildItem -Path "${{ github.workspace }}\wolfssl" -Recurse -Filter "wolfssl.dll" -ErrorAction SilentlyContinue | Select-Object -First 1
+        if ($wolfsslDll -and -not (Test-Path (Join-Path $sshdDir "wolfssl.dll"))) {
+            Copy-Item -Path $wolfsslDll.FullName -Destination (Join-Path $sshdDir "wolfssl.dll") -Force
+        }
+
+    - name: Test LoginGraceTime enforcement on Windows
+      working-directory: ${{ github.workspace }}\wolfssh\apps\wolfsshd\test
+      shell: pwsh
+      timeout-minutes: 2
+      run: pwsh -File .\sshd_login_grace_test.ps1 -SshdExe "$env:SSHD_PATH"
+
diff --git a/apps/wolfsshd/test/run_all_sshd_tests.sh b/apps/wolfsshd/test/run_all_sshd_tests.sh
@@ -132,7 +132,6 @@ else
 
     #Github actions needs resolved for these test cases
     #run_test "error_return.sh"
-    #run_test "sshd_login_grace_test.sh"
 
     # add additional tests here, check on var USING_LOCAL_HOST if can make sshd
     # server start/restart with changes
@@ -147,9 +146,10 @@ else
         run_test "sshd_forcedcmd_test.sh"
         run_test "sshd_window_full_test.sh"
         run_test "sshd_empty_password_test.sh"
+        run_test "sshd_login_grace_test.sh"
     else
         printf "Skipping tests that need to setup local SSHD\n"
-        SKIPPED=$((SKIPPED+3))
+        SKIPPED=$((SKIPPED+4))
     fi
 
     # these tests run with X509 sshd-config loaded

diff --git a/apps/wolfsshd/test/sshd_login_grace_test.ps1 b/apps/wolfsshd/test/sshd_login_grace_test.ps1
@@ -0,0 +1,129 @@
+#!/usr/bin/env pwsh
+#
+# Windows regression test for wolfsshd LoginGraceTime enforcement.
+#
+# Opens a raw TCP connection that never authenticates and verifies that
+# wolfsshd drops it at the login grace deadline. No Windows user account or
+# authorized key is required, because the connection is closed before
+# authentication ever completes - this exercises the pre-auth grace timer only.
+#
+# Enforcement is checked behaviorally (the server closes the connection at the
+# grace deadline), not by reading the daemon log, so the test does not depend on
+# debug logging being compiled into the wolfSSH Windows build.
+#
+# Usage:
+#   pwsh sshd_login_grace_test.ps1 -SshdExe <path-to-wolfsshd.exe> [-Port N] [-Grace N]
+#   (SshdExe also accepts the SSHD_PATH environment variable.)
+
+param(
+    [string]$SshdExe = $env:SSHD_PATH,
+    [int]$Port = 22224,
+    [int]$Grace = 5
+)
+
+$ErrorActionPreference = "Stop"
+$exitCode = 1
+
+$scriptDir = Split-Path -Parent $MyInvocation.MyCommand.Path
+$repoRoot  = (Resolve-Path (Join-Path $scriptDir "..\..\..")).Path
+$keyPath   = (Resolve-Path (Join-Path $repoRoot "keys\server-key.pem")).Path
+$confFile  = Join-Path $scriptDir "sshd_config_test_login_grace"
+$authFile  = Join-Path $scriptDir "authorized_keys_test"
+
+if (-not $SshdExe -or -not (Test-Path $SshdExe)) {
+    Write-Host "ERROR: wolfsshd.exe not found (pass -SshdExe or set SSHD_PATH)"
+    exit 1
+}
+
+@"
+Port $Port
+Protocol 2
+LoginGraceTime $Grace
+PermitRootLogin yes
+PasswordAuthentication yes
+PermitEmptyPasswords no
+UseDNS no
+HostKey $keyPath
+AuthorizedKeysFile $authFile
+"@ | Out-File -FilePath $confFile -Encoding ASCII
+
+"" | Out-File -FilePath $authFile -Encoding ASCII
+
+# Run wolfsshd in the foreground (-D selects the non-service path on Windows).
+$sshd = Start-Process -FilePath $SshdExe `
+    -ArgumentList "-D", "-f", "`"$confFile`"", "-p", "$Port" `
+    -NoNewWindow -PassThru
+
+try {
+    # Wait for the listener to accept connections.
+    $up = $false
+    for ($i = 0; $i -lt 20; $i++) {
+        try {
+            $probe = New-Object System.Net.Sockets.TcpClient
+            $probe.Connect("127.0.0.1", $Port)
+            $probe.Close()
+            $up = $true
+            break
+        }
+        catch {
+            Start-Sleep -Milliseconds 500
+        }
+    }
+    if (-not $up) {
+        # throw rather than exit so the finally block still stops the daemon
+        throw "wolfsshd did not start listening on port $Port"
+    }
+
+    # Open a raw TCP connection and never authenticate. The server sends its
+    # banner, waits for ours, and must close the connection once the login grace
+    # time expires. Block on Read (with a timeout well past the grace time) and
+    # measure when the server closes the connection.
+    $stall = New-Object System.Net.Sockets.TcpClient
+    $stall.Connect("127.0.0.1", $Port)
+    $stream = $stall.GetStream()
+    $stream.ReadTimeout = ($Grace + 5) * 1000
+
+    $buf = New-Object byte[] 4096
+    $dropped = $false
+    $sw = [System.Diagnostics.Stopwatch]::StartNew()
+    try {
+        while ($true) {
+            $n = $stream.Read($buf, 0, $buf.Length)
+            if ($n -le 0) {
+                $dropped = $true   # server closed the connection
+                break
+            }
+            # otherwise the server sent its banner; keep waiting for the drop
+        }
+    }
+    catch [System.IO.IOException] {
+        # Read timed out: the connection was still open past the grace time.
+        $dropped = $false
+    }
+    $elapsed = [math]::Round($sw.Elapsed.TotalSeconds, 1)
+    $stall.Close()
+
+    Write-Host "connection closed=$dropped after ${elapsed}s (grace=$Grace)"
+
+    if ($dropped -and ($elapsed -ge ($Grace - 1)) -and ($elapsed -le ($Grace + 4))) {
+        Write-Host "PASS: unauthenticated connection dropped at login grace deadline"
+        $exitCode = 0
+    }
+    elseif ($dropped) {
+        Write-Host "FAIL: connection closed at ${elapsed}s, not near the grace deadline ($Grace s)"
+    }
+    else {
+        Write-Host "FAIL: connection still open past the grace time (not enforced)"
+    }
+}
+catch {
+    Write-Host "ERROR: $_"
+    $exitCode = 1
+}
+finally {
+    if ($sshd -and -not $sshd.HasExited) {
+        Stop-Process -Id $sshd.Id -Force -ErrorAction SilentlyContinue
+    }
+}
+
+exit $exitCode
diff --git a/apps/wolfsshd/test/sshd_login_grace_test.sh b/apps/wolfsshd/test/sshd_login_grace_test.sh
@@ -47,18 +47,53 @@ if [ "$RESULT" != 0 ]; then
     exit 1
 fi
 
-# attempt clearing out stdin from previous echo/grep
-read -t 1 -n 1000 discard
+popd
 
-# test grace login timeout by stalling on password prompt
-timeout --foreground 7 "$TEST_CLIENT" -u "$USER" -h "$TEST_HOST" -p "$TEST_PORT" -t
+# Test the grace-time timeout behaviorally: open a raw TCP connection, never
+# authenticate, and confirm the server closes it at the grace deadline. This
+# asserts the actual behavior rather than scraping the log, matching the Windows
+# PowerShell test (and not relying on the daemon log being readable).
+GRACE=5
+exec 3<>"/dev/tcp/$TEST_HOST/$TEST_PORT"
+if [ "$?" != 0 ]; then
+    echo "FAIL: could not connect to $TEST_HOST:$TEST_PORT"
+    exit 1
+fi
 
-popd
-cat ./log.txt | grep "Failed login within grace period"
-RESULT=$?
-if [ "$RESULT" != 0 ]; then
-    echo "FAIL: Grace period not hit"
-    cat ./log.txt
+# The server sends its banner, waits for ours (which never comes), then closes
+# the connection once the grace time expires. Read until the server closes the
+# connection (EOF) or the per-read timeout elapses, and measure how long it
+# took. Use a large read timeout (GRACE + 8) and decide by elapsed time rather
+# than read's exit status, which differs across bash versions (timeout returns
+# >128 on modern bash but 1 on the macOS bash 3.2).
+START=$SECONDS
+while true; do
+    if IFS= read -r -t $((GRACE + 8)) -n 1024 _ <&3; then
+        : # received banner/data, keep waiting for the server to close
+    else
+        break # server closed (EOF) or the read timeout elapsed
+    fi
+done
+ELAPSED=$((SECONDS - START))
+exec 3>&-
+
+# An exit well before the read timeout means the server closed the connection;
+# an exit near GRACE + 8 means it stayed open (not enforced).
+if [ "$ELAPSED" -le $((GRACE + 4)) ]; then
+    DROPPED=1
+else
+    DROPPED=0
+fi
+
+echo "connection closed=$DROPPED after ${ELAPSED}s (grace=$GRACE)"
+
+if [ "$DROPPED" = 1 ] && [ "$ELAPSED" -ge $((GRACE - 1)) ]; then
+    echo "PASS: unauthenticated connection dropped at login grace deadline"
+elif [ "$DROPPED" = 1 ]; then
+    echo "FAIL: connection closed at ${ELAPSED}s, before the grace deadline ($GRACE s)"
+    exit 1
+else
+    echo "FAIL: connection still open past the grace time (not enforced)"
     exit 1
 fi