Private/CertificateChecks.ps1

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109
110
111
112
113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135
136
137
138
139
140
141
142
143
144
145
146
147
148
149
150
151
152
153
154
155
156
157
158
159
160
161
162
163
164
165
166
167
168
169
170
171
172
173
174
175
176
177
178
179
180
181
182
183
184
185
186
187
188
189
190
191
192
193
194
195
196
197
198
199
200
201
202
203
204
205
206
207
208
209
210
211
212
213
214
215
216
217
218
219
220
221
222
223
224
225
226
227
228
229
230
231
232
233
234
235
236
237
238
239
240
241
242
243
244
245
246
247
248
249
250
251
252
253
254
255
256
257
258
259
260
261
262
263
264
265
266
267
268
269
270
271
272
273
274
275
276
277
278
279
280
281
282
283
284
285
286
287
288
289
290
291
292
293
294
295
296
297
298
299
300
301
302
303
304
305
306
307
308
309
310
311
312
313
314
315
316
317
318
319
320
321
322
323
324
325
326
327
328
329
330
331
332
333
334
335
336
337
338
339
340
341
342
343
344
345
346
347
348
349
350
Function Test-CertificateAvailable
{
    param(
        $adfsCertificate, # Single element of list Generated by Get-AdfsCertificatesToTest
        [string]
        $certificateType,
        [bool]
        $isPrimary = $true,
        [string]
        $notRunReason
    )

    $testName = Create-CertCheckName -certType $certificateType -checkName "NotFoundInStore" -isPrimary $isPrimary

    if (-not $adfsCertificate -and [String]::IsNullOrEmpty($notRunReason))
    {
        $notRunReason = "Certificate object is null."
    }

    if (-not [String]::IsNullOrEmpty($notRunReason))
    {
        return Create-CertificateCheckResult -cert $null -testName $testName -result NotRun -detail $notRunReason
    }

    try
    {
        $thumbprint = $adfsCertificate.Thumbprint
        $testResult = New-Object TestResult -ArgumentList($testName)
        $testResult.Result = [ResultType]::NotRun;
        $testResult.Output = @{$tpKey = $thumbprint}

        if ($adfsCertificate.StoreLocation -eq "LocalMachine")
        {
            $certStore = New-Object System.Security.Cryptography.X509Certificates.X509Store($adfsCertificate.StoreName, `
                    [System.Security.Cryptography.X509Certificates.StoreLocation]::LocalMachine)
            try
            {
                $certStore.Open("IncludeArchived")

                $certSearchResult = $certStore.Certificates | where {$_.Thumbprint -eq $thumbprint}
                if (($certSearchResult | measure).Count -eq 0)
                {
                    $testResult.Detail = "$certificateType certificate with thumbprint $thumbprint not found in LocalMachine\{0} store.`n" -f $adfsCertificate.StoreName
                    $testResult.Result = [ResultType]::Fail
                }
                else
                {
                    $testResult.Result = [ResultType]::Pass
                }
            }
            catch
            {
                $testResult.Result = [ResultType]:: NotRun;
                $testResult.Detail = "$certificateType certificate with thumbprint $thumbprint encountered exception with message`n" + $_.Exception.Message
            }
            finally
            {
                $certStore.Close()
            }
        }
        else
        {
            $testResult.Result = [ResultType]:: NotRun;
            $testResult.Detail = "$certificateType certificate with thumbprint $thumbprint not checked for availability because it is in store: " + $adfsCertificate.StoreLocation
        }

        return $testResult
    }
    catch [Exception]
    {
        return Create-ErrorExceptionTestResult $testName $_.Exception
    }
}

function Test-CertificateExpired
{
    param (
        [System.Security.Cryptography.X509Certificates.X509Certificate2]
        $cert,
        [string]
        $certificateType,
        [bool]
        $isPrimary = $true,
        [string]
        $notRunReason
    )

    $checkName = "Expired"

    $testName = Create-CertCheckName -certType $certificateType -checkName $checkName -isPrimary $isPrimary

    if (-not $cert -and [String]::IsNullOrEmpty($notRunReason))
    {
        $notRunReason = "Certificate object is null."
    }
    if (-not [String]::IsNullOrEmpty($notRunReason))
    {
        return Create-CertificateCheckResult -cert $null -testName $testName -result NotRun -detail $notRunReason
    }

    try
    {
        if (Verify-IsCertExpired -cert $cert)
        {
            $tp = $cert.Thumbprint

            $certificateExpiredTestDetail = "$certificateType certificate with thumbprint $tp has expired.`n";
            $certificateExpiredTestDetail += "Valid From: " + $cert.NotBefore.ToString() + "`nValid To: " + $cert.NotAfter.ToString();
            $certificateExpiredTestDetail += "`nAutoCertificateRollover Enabled: " + (Retrieve-AdfsProperties).AutoCertificateRollover + "`n";
            return Create-CertificateCheckResult -cert $cert -testName $testName -result Fail -detail $certificateExpiredTestDetail
        }
        else
        {
            return Create-CertificateCheckResult -cert $cert -testName $testName -result Pass
        }
    }
    catch [Exception]
    {
        return Create-ErrorExceptionTestResult $testName $_.Exception
    }
}

function Test-CertificateAboutToExpire
{

    param (
        [System.Security.Cryptography.X509Certificates.X509Certificate2]
        $cert,
        [string]
        $certificateType,
        [bool]
        $isPrimary = $true,
        [string]
        $notRunReason
    )
    $checkName = "AboutToExpire"

    $testName = Create-CertCheckName -certType $certificateType -checkName $checkName -isPrimary $isPrimary

    $expiryLimitInDays = 90;

    if (-not $cert -and [String]::IsNullOrEmpty($notRunReason))
    {
        $notRunReason = "Certificate object is null."
    }
    if (-not [String]::IsNullOrEmpty($notRunReason))
    {
        return Create-CertificateCheckResult -cert $null -testName $testName -result NotRun -detail $notRunReason
    }

    try
    {
        $properties = Retrieve-AdfsProperties
        if ($properties.AutoCertificateRollover -and ($certificateType -eq "Token-Decrypting" -or $certificateType -eq "Token-Signing"))
        {
            return Create-CertificateCheckResult -cert $cert -testName $testName -result NotRun -detail "Check Skipped when AutoCertificateRollover is enabled"
        }

        $expirtyMinusToday = [System.Convert]::ToInt32(($cert.NotAfter - (Get-Date)).TotalDays);
        if ($expirtyMinusToday -le $expiryLimitInDays)
        {
            $tp = $cert.Thumbprint

            $certificateAboutToExpireTestDetail = "$certificateType certificate with thumbprint $tp is about to expire in $expirtyMinusToday days.`n"
            $certificateAboutToExpireTestDetail += "Valid From: " + $cert.NotBefore.ToString() + "`nValid To: " + $cert.NotAfter.ToString();
            $certificateAboutToExpireTestDetail += "`nAutoCertificateRollover Enabled: " + (Retrieve-AdfsProperties).AutoCertificateRollover + "`n";
            return Create-CertificateCheckResult -cert $cert -testName $testName -result Fail -detail $certificateAboutToExpireTestDetail
        }
        else
        {
            return Create-CertificateCheckResult -cert $cert -testName $testName -result Pass
        }
    }
    catch [Exception]
    {
        return Create-ErrorExceptionTestResult $testName $_.Exception
    }
}

function Test-CertificateHasPrivateKey
{
    param (
        [System.Security.Cryptography.X509Certificates.X509Certificate2]
        $cert,
        [string]
        $certificateType,
        [bool]
        $isPrimary = $true,
        [string]
        $storeName,
        [string]
        $storeLocation,
        [string]
        $notRunReason
    )

    $checkName = "PrivateKeyAbsent"

    $testName = Create-CertCheckName -certType $certificateType -checkName $checkName -isPrimary $isPrimary

    if (-not $cert -and [String]::IsNullOrEmpty($notRunReason))
    {
        $notRunReason = "Certificate object is null."
    }

    if (-not [String]::IsNullOrEmpty($notRunReason))
    {
        return Create-CertificateCheckResult -cert $null -testName $testName -result NotRun -detail $notRunReason
    }

    try
    {
        $properties = Retrieve-AdfsProperties
        if ($properties.AutoCertificateRollover -and ($certificateType -eq "Token-Decrypting" -or $certificateType -eq "Token-Signing"))
        {
            return Create-CertificateCheckResult -cert $cert -testName $testName -result NotRun -detail "Check Skipped when AutoCertificateRollover is enabled"
        }

        #special consideration to the corner case where auto certificate rollover was on, then turned off, leaving behind some certificates in the CU\MY store
        #in which case, we cannot ascertain whether the private key is present or not
        if ($storeLocation -eq "CurrentUser")
        {
            return Create-CertificateCheckResult -cert $cert -testName $testName -result NotRun -detail "Check Skipped because the certificate is in the CU\MY store"
        }

        if ($cert.HasPrivateKey)
        {
            return Create-CertificateCheckResult -cert $cert -testName $testName -result Pass
        }
        else
        {
            $tp = $cert.Thumbprint
            $detail = "$certificateType certificate with thumbprint $tp does not have a private key."
            return Create-CertificateCheckResult -cert $cert -testName $testName -result Fail -detail $detail
        }
    }
    catch [Exception]
    {
        return Create-ErrorExceptionTestResult $testName $_.Exception
    }
}

function Test-CertificateSelfSigned
{
    param (
        [System.Security.Cryptography.X509Certificates.X509Certificate2]
        $cert,
        [string]
        $certificateType,
        [bool]
        $isPrimary = $false,
        [string]
        $notRunReason
    )

    $checkName = "IsSelfSigned"

    $testName = Create-CertCheckName -certType $certificateType -checkName $checkName -isPrimary $isPrimary

    if (-not $cert -and [String]::IsNullOrEmpty($notRunReason))
    {
        $notRunReason = "Certificate object is null."
    }

    if (-not [String]::IsNullOrEmpty($notRunReason))
    {
        return Create-CertificateCheckResult -cert $null -testName $testName -result NotRun -detail $notRunReason
    }

    try
    {
        $properties = Retrieve-AdfsProperties
        if ($properties.AutoCertificateRollover -and ($certificateType -eq "Token-Decrypting" -or $certificateType -eq "Token-Signing"))
        {
            return Create-CertificateCheckResult -cert $cert -testName $testName -result NotRun -detail "Check Skipped when AutoCertificateRollover is enabled"
        }
        if (Verify-IsCertSelfSigned $cert)
        {
            $tp = $cert.Thumbprint
            $detail = "$certificateType certificate with thumbprint $tp is self-signed."
            return Create-CertificateCheckResult -cert $cert -testName $testName -result Fail -detail $detail
        }
        else
        {
            return Create-CertificateCheckResult -cert $cert -testName $testName -result Pass
        }
    }
    catch [Exception]
    {
        return Create-ErrorExceptionTestResult $testName $_.Exception
    }
}

function Test-CertificateCRL
{
    param (
        [System.Security.Cryptography.X509Certificates.X509Certificate2]
        $cert,
        [string]
        $certificateType,
        [bool]
        $isPrimary = $false,
        [string]
        $notRunReason
    )

    $checkName = "Revoked"
    $chainStatusKey = "ChainStatus"

    $testName = Create-CertCheckName -certType $certificateType -checkName $checkName -isPrimary $isPrimary

    if (-not $cert -and [String]::IsNullOrEmpty($notRunReason))
    {
        $notRunReason = "Certificate object is null."
    }

    if (-not [String]::IsNullOrEmpty($notRunReason))
    {
        return Create-CertificateCheckResult -cert $null -testName $testName -result NotRun -detail $notRunReason
    }

    try
    {
        $crlResult = VerifyCertificateCRL -cert $cert
        $passFail = [ResultType]::Pass
        if (($crlResult.ChainBuildResult -eq $false) -and ($crlResult.IsSelfSigned -eq $false))
        {
            $passFail = [ResultType]::Fail
        }
        $testResult = Create-CertificateCheckResult -cert $cert -testName $testName -result $passFail
        $testDetail = "Thumbprint: " + $crlResult.Thumbprint + "`n"

        $testResult.Output.Add($chainStatusKey, "NONE")
        if ($crlResult.ChainStatus)
        {
            $testResult.Output.Set_Item($chainStatusKey, $crlResult.ChainStatus)
            foreach ($chainStatus in $crlResult.ChainStatus)
            {
                $testDetail = $testDetail + $chainStatus.Status + "-" + $chainStatus.StatusInformation + [System.Environment]::NewLine
            }
        }

        $testResult.Detail = $testDetail
        return $testResult
    }
    catch [Exception]
    {
        return Create-ErrorExceptionTestResult $testName $_.Exception
    }
}