# Permanent error "5.3.3 Command not implemented"

**URL:** <https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559>\
**Category:** Mutual Help\
**Tags:** android\
**Created:** [March 4, 2021, 8:29pm UTC](https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559 "2021-03-04T20:29:44Z")\
**Posts on this page:** 7\
**Page:** 1

<div class="post-metadata">

**Author:** ![mbeko](https://support.delta.chat/user_avatar/support.delta.chat/mbeko/32/175_2.png) [@mbeko](https://support.delta.chat/u/mbeko)\
**Post date:** [March 4, 2021, 8:29pm UTC](https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559/1 "2021-03-04T20:29:44Z")

</div>

**Delta Chat version**

1.14.5

**Expected behavior**

Message is sent as indicated by a green checkmark at the bottom right of the message.

**Actual behavior**

A cross symbol instead of a checkmark indicates that the message has not been sent.

Below the message is an info box saying “permanent: 5.3.3 Command not implemented”.

**Steps to reproduce the problem**

I wanted to send a regular message to a contact as I had done without problems two weeks earlier.

I haven’t updated Delta Chat or changed the configuration in the meantime.  
I only switched to a second account at some point and switched back today.

It fails also for other contacts, even in “Saved messages”.

As I understand the description on the mail provider’s page, it’s a Microsoft server:

> The mailboxes of a mail domain are hosted on a central Exchange system

However, sending mails from Thunderbird and K-9 Mail works with that account as usual.  
There are also no issues in Delta Chat with the second account which is on a completely different server.

I’m aware that it’s therefore probably a server issue. I don’t know what to make of the error message, though – which is the unimplemented command and why is it suddenly a problem? I also wonder why it doesn’t appear in the other e-mail applications.

**Debug logs**

> **Logs**
>
> ```plaintext
> 03-04 20:22:28.069 5237 12544 W DeltaChat: src/job.rs:254: SMTP failed to send: permanent: 5.3.3 Command not implemented
> 03-04 20:22:28.069 5237 12544 W DeltaChat: src/message.rs:1500: Msg#445 failed: permanent: 5.3.3 Command not implemented
> 03-04 20:22:28.100 5237 12544 I DeltaChat: src/job.rs:1100: Finished immediate try 0 of job #387, action SendMsgToSmtp
> 03-04 20:22:28.100 5237 12544 W DeltaChat: src/job.rs:1052: Smtp removes job #387, action SendMsgToSmtp as it failed with error Permanent SMTP error: permanent: 5.3.3 Command not implemented
> 
> ```

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<div class="post-metadata">

**Author:** ![link2xt](https://support.delta.chat/user_avatar/support.delta.chat/link2xt/32/1971_2.png) [@link2xt](https://support.delta.chat/u/link2xt)\
**Post date:** [March 5, 2021, 12:35am UTC](https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559/2 "2021-03-05T00:35:22Z")

</div>

If you use Linux, I can give instructions on how to run command-line client with SMTP logs enabled.

My guess is that command not implemented is `STARTTLS`. You can try to fix the problem by going into “Settings” → Your avatar → “Password and account” and clicking the tickmark without changing anything. This will run autoconfiguration again and, if succeeds, overwrite your configuration with a new working one.

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<div class="post-metadata">

**Author:** ![mbeko](https://support.delta.chat/user_avatar/support.delta.chat/mbeko/32/175_2.png) [@mbeko](https://support.delta.chat/u/mbeko)\
**Post date:** [March 6, 2021, 5:24pm UTC](https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559/3 "2021-03-06T17:24:06Z")

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Thanks, I do use Linux and those instructions would be highly welcome.

I had already tried the different SMTP security settings. None of them worked and after going back to the initial _Automatic_ option, the error still appears.

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<div class="post-metadata">

**Author:** ![link2xt](https://support.delta.chat/user_avatar/support.delta.chat/link2xt/32/1971_2.png) [@link2xt](https://support.delta.chat/u/link2xt)\
**Post date:** [March 8, 2021, 4:32am UTC](https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559/4 "2021-03-08T04:32:55Z")

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You need to install `git` (`sudo apt-get install git`) and Rust (from [https://rustup.rs/](https://rustup.rs/) with a command `curl --proto '=https' --tlsv1.2 -sSf https://sh.rustup.rs | sh -s -- -y --default-toolchain none` running as normal non-root user).

Then clone [GitHub - deltachat/deltachat-core-rust: Delta Chat Rust Core library, used by Android/iOS/desktop apps and bindings](https://github.com/deltachat/deltachat-core-rust/) repository with `git clone https://github.com/deltachat/deltachat-core-rust.git`. In the folder with `deltachat-core-rust` source code, run `RUST_LOG=info,async_smtp=trace cargo run --example repl --features repl -- deltachat.db`. This will compile and run command-line client (REPL, Read-Eval-Print-Loop) with SMTP tracing enabled. There, run the command `import-backup your-backup-file.bak` and then `configure`. Or, instead of importing backup, run `set addr your-address`, `set mail_pw your-password` and then `configure`.

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<div class="post-metadata">

**Author:** ![mbeko](https://support.delta.chat/user_avatar/support.delta.chat/mbeko/32/175_2.png) [@mbeko](https://support.delta.chat/u/mbeko)\
**Post date:** [March 14, 2021, 7:46pm UTC](https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559/5 "2021-03-14T19:46:27Z")

</div>

Thanks, that worked. Can you read something out of these debug messages?

> **REPL log output**
>
> ```nohighlight
> > send test
> > INFO repl > Received NewBlobFile("$BLOBDIR/${id}")
> INFO repl > src/job.rs:200: saving job for Smtp-thread: Job { job_id: 0, action: SendMsgToSmtp, foreign_id: 109, desired_timestamp: 1615752864, added_timestamp: 1615752864, tries: 0, param: Params { inner: {Recipients: "${address}", File: "$BLOBDIR/${id}"} }, pending_error: None }
> INFO repl > src/job.rs:1238: interrupt: smtp
> INFO repl > Received MSGS_CHANGED(chat_id=Chat#10, msg_id=Msg#109)
> INFO repl > src/scheduler.rs:261: smtp fake idle - interrupted
> INFO repl > src/job.rs:1270: loading job for Smtp-thread
> INFO repl > src/scheduler.rs:253: executing smtp job
> INFO repl > src/job.rs:1075: Smtp-job #32, action SendMsgToSmtp started...
> INFO repl > src/job.rs:1144: Smtp begin immediate try 0 of job #32, action SendMsgToSmtp
> DEBUG async_smtp::smtp::client::inner > << 220 ${host} Microsoft ESMTP MAIL Service ready at Sun, 14 Mar 2021 21:14:23 +0100<CRLF>
> DEBUG async_smtp::smtp::smtp_client > connection established to ${ip_1}:587
> DEBUG async_smtp::smtp::client::inner > >> EHLO [127.0.0.1]<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-AUTH GSSAPI NTLM<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-AUTH GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-AUTH GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-AUTH GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-STARTTLS<CRLF>250-AUTH GSSAPI NTLM<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250 SMTPUTF8<CRLF>
> DEBUG async_smtp::smtp::smtp_client > server ${host} with {EightBitMime, SmtpUtfEight, StartTls}
> DEBUG async_smtp::smtp::client::inner > >> STARTTLS<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 220 2.0.0 SMTP server ready<CRLF>
> DEBUG async_smtp::smtp::smtp_client > connection encrypted
> DEBUG async_smtp::smtp::client::inner > >> EHLO [127.0.0.1]<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH GSSAPI NTLM LOGIN<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH GSSAPI NTLM LOGIN<CRLF>250-8BITMIME<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH GSSAPI NTLM LOGIN<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH GSSAPI NTLM LOGIN<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 250-${host} Hello [${ip_2}]<CRLF>250-SIZE 41943040<CRLF>250-PIPELINING<CRLF>250-DSN<CRLF>250-ENHANCEDSTATUSCODES<CRLF>250-AUTH GSSAPI NTLM LOGIN<CRLF>250-8BITMIME<CRLF>250-BINARYMIME<CRLF>250-CHUNKING<CRLF>250 SMTPUTF8<CRLF>
> DEBUG async_smtp::smtp::smtp_client > server ${host} with {Authentication(Login), SmtpUtfEight, EightBitMime}
> DEBUG async_smtp::smtp::client::inner > >> AUTH LOGIN<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 334 ${string_1}<CRLF>
> DEBUG async_smtp::smtp::commands > auth encoded challenge: ${string_1}
> DEBUG async_smtp::smtp::commands > auth decoded challenge: Username:
> DEBUG async_smtp::smtp::client::inner > >> ${string_2}=<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 334 ${string_3}<CRLF>
> DEBUG async_smtp::smtp::commands > auth encoded challenge: ${string_3}
> DEBUG async_smtp::smtp::commands > auth decoded challenge: Password:
> DEBUG async_smtp::smtp::client::inner > >> ${string_4}==<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 235 2.7.0 Authentication successful<CRLF>
> INFO repl > [SMTP_CONNECTED] SMTP-LOGIN as ${address} ok
> DEBUG async_smtp::smtp::client::inner > >> MAIL FROM:<${address}> BODY=8BITMIME SMTPUTF8<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 502 5.3.3 Command not implemented<CRLF>
> DEBUG async_smtp::smtp::client::inner > >> QUIT<CRLF>
> DEBUG async_smtp::smtp::client::inner > << 221 2.0.0 Service closing transmission channel<CRLF>
> WARN repl > src/job.rs:256: SMTP failed to send: permanent: 5.3.3 Command not implemented
> WARN repl > src/message.rs:1676: Msg#109 failed: Permanent SMTP error: permanent: 5.3.3 Command not implemented
> INFO repl > Received MsgFailed { chat_id: ChatId(10), msg_id: MsgId(109) }
> INFO repl > src/job.rs:1168: Finished immediate try 0 of job #32, action SendMsgToSmtp
> WARN repl > src/job.rs:1120: Smtp removes job #32, action SendMsgToSmtp as it failed with error Permanent SMTP error: permanent: 5.3.3 Command not implemented
> 
> ```

---

<div class="post-metadata">

**Author:** ![link2xt](https://support.delta.chat/user_avatar/support.delta.chat/link2xt/32/1971_2.png) [@link2xt](https://support.delta.chat/u/link2xt)\
**Post date:** [March 14, 2021, 9:57pm UTC](https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559/6 "2021-03-14T21:57:15Z")

</div>

Looks like the server advertises `8BITMIME` and `SMTPUTF8` in response to `EHLO`, but then rejects `MAIL FROM:<${address}> BODY=8BITMIME SMTPUTF8` after successful `STARTTLS` and `AUTH` with `502 5.3.3 Command not implemented`.

Looks like a bug in MS exchange, but I wonder why Thunderbird and K-9 work, they probably have some workaround for this.

---

<div class="post-metadata">

**Author:** ![mbeko](https://support.delta.chat/user_avatar/support.delta.chat/mbeko/32/175_2.png) [@mbeko](https://support.delta.chat/u/mbeko)\
**Post date:** [March 30, 2021, 8:43pm UTC](https://support.delta.chat/t/permanent-error-5-3-3-command-not-implemented/1559/7 "2021-03-30T20:43:04Z")

</div>

Thanks, I planned on researching about these advertised properties, but didn’t have much time in the recent weeks.

Fortunately, the problem “fixed itself” in the meantime. I can send messages as previously again without having done anything.

Thanks again for your hints!