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<a href="https://gitlab.com/samuel40791765">Samuel Chiang</a> created an issue: <a href="https://gitlab.com/gnutls/gnutls/-/issues/1632">#1632</a>
</p>
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<h2 dir="auto" style="margin-top: 0; margin-bottom: 1rem; border-bottom-style: solid; border-bottom-color: #dcdcde; font-weight: 600; font-size: clamp(1.3125rem, 0.8680555556rem + 0.9259259259vw, 1.5625rem); letter-spacing: -0.01em; line-height: 1.25; color: #18171d; border-bottom-width: 1px; padding-bottom: 0.25rem;" align="initial">
<a href="#description-of-problem" aria-hidden="true" class="anchor" id="user-content-description-of-problem" style="margin-top: 0; float: left; margin-left: -20px; text-decoration: none; outline: none;"></a>Description of problem:</h2>
<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">gnu-tls/certtool outputs a PKCS8 file that's not coherent with RFC8018 Appendix A.2: <a href="https://datatracker.ietf.org/doc/html/rfc8018#appendix-A.2" rel="nofollow noreferrer noopener" target="_blank" style="margin-top: 0;">https://datatracker.ietf.org/doc/html/rfc8018#appendix-A.2</a> The RFC states that the PBKDF2-PRF Algorithm identifier should have a NULL field paired with the algorithm id to be used.</p>
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<pre class="code highlight js-syntax-highlight language-plaintext" v-pre="true" style='display: block; font-size: 14px; color: #3a383f; line-height: 1.6em; overflow-x: auto; border-radius: .25rem; position: relative; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; word-break: break-all; word-wrap: break-word; background-color: #fbfafd; margin: 0 0 1rem; padding: 12px; border: 1px solid #dcdcde;'><code style='font-size: inherit; color: inherit; word-wrap: normal; word-break: keep-all; border-radius: .25rem; background-color: inherit; white-space: pre; margin-top: 0; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; overflow-wrap: normal; padding: unset;'><span id="LC1" class="line" lang="plaintext" style="margin-top: 0;"> algid-hmacWithSHA1 AlgorithmIdentifier {{PBKDF2-PRFs}} ::=</span>
<span id="LC2" class="line" lang="plaintext"> {algorithm id-hmacWithSHA1, parameters NULL : NULL}</span></code></pre>
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<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">The pkcs8 files I've generated with gnu-tls using <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; margin-top: 0; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>PBES2_AES_128</code> are missing this NULL field, which causes a parsing error in <a href="https://github.com/aws/aws-lc/blob/f45bc34b9132fbd7749c45431fa06a89198cdb4b/crypto/pkcs8/p5_pbev2.c#L292-L300" rel="nofollow noreferrer noopener" target="_blank">AWS-LC</a> & <a href="https://github.com/google/boringssl/blob/be21ef7012f0812bb1c0c8fc226979fa6c301e8d/crypto/pkcs8/p5_pbev2.cc#L292-L300" rel="nofollow noreferrer noopener" target="_blank">BoringSSL</a> due to their stricter checks.
Just as additional sanity test, the PKCS8 files I've generated with OpenSSL don't have this issue and correctly generate a PKCS8 file with the NULL field paired with the algorithm id.</p>
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<li style="margin-top: 0; line-height: 1.6em; margin-left: 25px; padding-left: 3px;">OpenSSL command: <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; margin-top: 0; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>openssl pkcs8 -in rsa_key_file.pem -topk8 -v2 aes-128-cbc -out output.p8 -passout pass:abcedf</code>
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<h3 dir="auto" style="margin-top: 1.5rem; margin-bottom: 1rem; font-weight: 600; font-size: clamp(1.125rem, 0.9027777778rem + 0.462962963vw, 1.25rem); letter-spacing: inherit; line-height: 1.25; color: #18171d;" align="initial">
<a href="#side-note" aria-hidden="true" class="anchor" id="user-content-side-note" style="margin-top: 0; float: left; margin-left: -20px; text-decoration: none; outline: none;"></a>Side note:</h3>
<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">When running <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; margin-top: 0; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>certtool --to-p8 ... pkcs-cipher=...</code>, is <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>PKCS12_3DES_SHA1</code> the intended default? I noticed that there was this older commit 14 years ago that tried changing the default to <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>AES-128</code>: <a href="https://gitlab.com/gnutls/gnutls/-/commit/0d004a210db5d220c896456a165c81264fa4454a" data-reference-type="commit" data-original="https://gitlab.com/gnutls/gnutls/-/commit/0d004a210db5d220c896456a165c81264fa4454a" data-link="false" data-link-reference="true" data-commit="0d004a210db5d220c896456a165c81264fa4454a" data-project="179611" data-container="body" data-placement="top" title="Changed the default pkcs-cipher to AES-128. Allowed specifying the 3des-pkcs12" class="gfm gfm-commit has-tooltip" style='font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; font-size: 95%;'>0d004a21</a>. That was changed a couple years later when some parts of <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>certtool</code> were reworked in <a href="https://gitlab.com/gnutls/gnutls/-/commit/d0ae20f780ac74857d70b4190166bf18195ef4d7" data-reference-type="commit" data-original="https://gitlab.com/gnutls/gnutls/-/commit/d0ae20f780ac74857d70b4190166bf18195ef4d7" data-link="false" data-link-reference="true" data-commit="d0ae20f780ac74857d70b4190166bf18195ef4d7" data-project="179611" data-container="body" data-placement="top" title="certtool uses libopts for command line parsing." class="gfm gfm-commit has-tooltip" style='font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; font-size: 95%;'>d0ae20f7</a>. <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>pkcs_cipher</code> in the certtool application code doesn't have a default value assigned, which causes the <a href="https://gitlab.com/gnutls/gnutls/-/blob/d0ae20f780ac74857d70b4190166bf18195ef4d7/lib/x509/privkey_pkcs8.c#L412-434">default <code style='font-size: 90%; color: inherit; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; margin-top: 0; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>PKCS12_3DES_SHA1</code> schema</a> to be used instead. There isn't any explicit documentation on what the default for <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>pkcs-cipher</code> is however, I was more or less genuinely curious since the behavior's slightly inconsistent with past release notes and the commit history.</p>
<h2 dir="auto" style="margin-top: 1.5rem; margin-bottom: 1rem; border-bottom-style: solid; border-bottom-color: #dcdcde; font-weight: 600; font-size: clamp(1.3125rem, 0.8680555556rem + 0.9259259259vw, 1.5625rem); letter-spacing: -0.01em; line-height: 1.25; color: #18171d; border-bottom-width: 1px; padding-bottom: 0.25rem;" align="initial">
<a href="#version-of-gnutls-used" aria-hidden="true" class="anchor" id="user-content-version-of-gnutls-used" style="margin-top: 0; float: left; margin-left: -20px; text-decoration: none; outline: none;"></a>Version of gnutls used:</h2>
<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">gnutls-cli 3.6.13</p>
<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">Although this issue still seems to exist in gnutls today when looking at the relevant code here: <a href="https://gitlab.com/gnutls/gnutls/-/blob/master/lib/x509/pkcs7-crypt.c#L1349-1363" style="margin-top: 0;">https://gitlab.com/gnutls/gnutls/-/blob/master/lib/x509/pkcs7-crypt.c#L1349-1363</a></p>
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<a href="#distributor-of-gnutls-eg-ubuntu-fedora-rhel" aria-hidden="true" class="anchor" id="user-content-distributor-of-gnutls-eg-ubuntu-fedora-rhel" style="margin-top: 0; float: left; margin-left: -20px; text-decoration: none; outline: none;"></a>Distributor of gnutls (e.g., Ubuntu, Fedora, RHEL)</h2>
<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">Ubuntu</p>
<h2 dir="auto" style="margin-top: 1.5rem; margin-bottom: 1rem; border-bottom-style: solid; border-bottom-color: #dcdcde; font-weight: 600; font-size: clamp(1.3125rem, 0.8680555556rem + 0.9259259259vw, 1.5625rem); letter-spacing: -0.01em; line-height: 1.25; color: #18171d; border-bottom-width: 1px; padding-bottom: 0.25rem;" align="initial">
<a href="#how-reproducible" aria-hidden="true" class="anchor" id="user-content-how-reproducible" style="margin-top: 0; float: left; margin-left: -20px; text-decoration: none; outline: none;"></a>How reproducible:</h2>
<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">Steps to Reproduce:</p>
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<li style="margin-top: 0; line-height: 1.6em; margin-left: 25px; padding-left: 3px;">Use a RSA private key to load into certtool and output a pkcs8 file:</li>
</ol>
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<pre class="code highlight js-syntax-highlight language-plaintext" v-pre="true" style='display: block; font-size: 14px; color: #3a383f; line-height: 1.6em; overflow-x: auto; border-radius: .25rem; position: relative; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; word-break: break-all; word-wrap: break-word; background-color: #fbfafd; margin: 0 0 1rem; padding: 12px; border: 1px solid #dcdcde;'><code style='font-size: inherit; color: inherit; word-wrap: normal; word-break: keep-all; border-radius: .25rem; background-color: inherit; white-space: pre; margin-top: 0; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; overflow-wrap: normal; padding: unset;'><span id="LC1" class="line" lang="plaintext" style="margin-top: 0;">certtool --load-privkey=rsa_key_file.pem --to-p8 --password=abcdef --pkcs-cipher=aes-128</span></code></pre>
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<li style="margin-top: 0; line-height: 1.6em; margin-left: 25px; padding-left: 3px;">There's a nifty tool called <a href="https://github.com/google/der-ascii" rel="nofollow noreferrer noopener" target="_blank" style="margin-top: 0;">der2ascii</a> that helps dump out all the ASN.1 contents of a file.</li>
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<pre class="code highlight js-syntax-highlight language-plaintext" v-pre="true" style='display: block; font-size: 14px; color: #3a383f; line-height: 1.6em; overflow-x: auto; border-radius: .25rem; position: relative; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; word-break: break-all; word-wrap: break-word; background-color: #fbfafd; margin: 0 0 1rem; padding: 12px; border: 1px solid #dcdcde;'><code style='font-size: inherit; color: inherit; word-wrap: normal; word-break: keep-all; border-radius: .25rem; background-color: inherit; white-space: pre; margin-top: 0; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; overflow-wrap: normal; padding: unset;'><span id="LC1" class="line" lang="plaintext" style="margin-top: 0;">der2ascii -pem -i their-old-rsa-key.pem > their-old-rsa.txt</span></code></pre>
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<a href="#actual-results" aria-hidden="true" class="anchor" id="user-content-actual-results" style="margin-top: 0; float: left; margin-left: -20px; text-decoration: none; outline: none;"></a>Actual results:</h2>
<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">These are the ASN.1 contents of the PBKDF2 identifier I got:</p>
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<pre class="code highlight js-syntax-highlight language-plaintext" v-pre="true" style='display: block; font-size: 14px; color: #3a383f; line-height: 1.6em; overflow-x: auto; border-radius: .25rem; position: relative; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; word-break: break-all; word-wrap: break-word; background-color: #fbfafd; margin: 0 0 1rem; padding: 12px; border: 1px solid #dcdcde;'><code style='font-size: inherit; color: inherit; word-wrap: normal; word-break: keep-all; border-radius: .25rem; background-color: inherit; white-space: pre; margin-top: 0; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; overflow-wrap: normal; padding: unset;'><span id="LC1" class="line" lang="plaintext" style="margin-top: 0;">SEQUENCE {</span>
<span id="LC2" class="line" lang="plaintext"> # PBKDF2</span>
<span id="LC3" class="line" lang="plaintext"> OBJECT_IDENTIFIER { 1.2.840.113549.1.5.12 }</span>
<span id="LC4" class="line" lang="plaintext"> SEQUENCE {</span>
<span id="LC5" class="line" lang="plaintext"> OCTET_STRING { `b1322c8a7ae134caf8a30533730606801d25` }</span>
<span id="LC6" class="line" lang="plaintext"> INTEGER { `0927c0` }</span>
<span id="LC7" class="line" lang="plaintext"> INTEGER { 16 }</span>
<span id="LC8" class="line" lang="plaintext"> SEQUENCE {</span>
<span id="LC9" class="line" lang="plaintext"> # hmacWithSHA256</span>
<span id="LC10" class="line" lang="plaintext"> OBJECT_IDENTIFIER { 1.2.840.113549.2.9 }</span>
<span id="LC11" class="line" lang="plaintext"> }</span>
<span id="LC12" class="line" lang="plaintext"> }</span>
<span id="LC13" class="line" lang="plaintext"> }</span></code></pre>
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<a href="#expected-results" aria-hidden="true" class="anchor" id="user-content-expected-results" style="margin-top: 0; float: left; margin-left: -20px; text-decoration: none; outline: none;"></a>Expected results:</h2>
<p dir="auto" style="color: #3a383f; margin: 0 0 1rem;" align="initial">These are the ASN.1 contents I got from OpenSSL. Notice the <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; margin-top: 0; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>NULL {}</code> field paired along with the <code style='font-size: 90%; color: #18171d; word-wrap: break-word; border-radius: .25rem; background-color: #ececef; font-weight: inherit; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; white-space: pre-wrap; overflow-wrap: break-word; word-break: keep-all; padding: 0.125rem 0.25rem;'>hmacWithSHA256</code> OID.</p>
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<pre class="code highlight js-syntax-highlight language-plaintext" v-pre="true" style='display: block; font-size: 14px; color: #3a383f; line-height: 1.6em; overflow-x: auto; border-radius: .25rem; position: relative; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; word-break: break-all; word-wrap: break-word; background-color: #fbfafd; margin: 0 0 1rem; padding: 12px; border: 1px solid #dcdcde;'><code style='font-size: inherit; color: inherit; word-wrap: normal; word-break: keep-all; border-radius: .25rem; background-color: inherit; white-space: pre; margin-top: 0; font-family: "GitLab Mono", "JetBrains Mono", "Menlo", "DejaVu Sans Mono", "Liberation Mono", "Consolas", "Ubuntu Mono", "Courier New", "andale mono", "lucida console", monospace; font-variant-ligatures: none; overflow-wrap: normal; padding: unset;'><span id="LC1" class="line" lang="plaintext" style="margin-top: 0;"> SEQUENCE {</span>
<span id="LC2" class="line" lang="plaintext"> # PBKDF2</span>
<span id="LC3" class="line" lang="plaintext"> OBJECT_IDENTIFIER { 1.2.840.113549.1.5.12 }</span>
<span id="LC4" class="line" lang="plaintext"> SEQUENCE {</span>
<span id="LC5" class="line" lang="plaintext"> OCTET_STRING { `5b57711e03a7c6bc` }</span>
<span id="LC6" class="line" lang="plaintext"> INTEGER { 2048 }</span>
<span id="LC7" class="line" lang="plaintext"> SEQUENCE {</span>
<span id="LC8" class="line" lang="plaintext"> # hmacWithSHA256</span>
<span id="LC9" class="line" lang="plaintext"> OBJECT_IDENTIFIER { 1.2.840.113549.2.9 }</span>
<span id="LC10" class="line" lang="plaintext"> NULL {}</span>
<span id="LC11" class="line" lang="plaintext"> }</span>
<span id="LC12" class="line" lang="plaintext"> }</span>
<span id="LC13" class="line" lang="plaintext"> }</span></code></pre>
<copy-code></copy-code><insert-code-snippet></insert-code-snippet>
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