The packages I see for Ubuntu 22.04 are all 3.x:

https://packages.ubuntu.com/search?keywords=libssl-dev

Are you sure you're using 22.04? Could there be a mismatch between the headers installed by libssl-dev and the actual installed version of OpenSSL?

- Mike

On 6/4/23 03:18, David Rodriguez wrote:
Thanks Nicky & Mike !
I have tried firstly what Nichy said and after all, the issue remains the same. Checking openssl version, I see that I have 1.1.1n from March 2022 which I think it is the standard for Ubuntu 22.0.4 .
Any other stuff to try?



El sáb, 3 jun 2023 a las 22:51, Michael Jumper (<[email protected] <mailto:[email protected]>>) escribió:

    On 6/3/23 12:10, Nick Couchman wrote:
     > On Sat, Jun 3, 2023 at 2:26 PM David Rodriguez <[email protected]
    <mailto:[email protected]>
     > <mailto:[email protected] <mailto:[email protected]>>> wrote:
     >
     >     I'm trying to upgrade to 1.5.2 in a Ubuntu 22.0.4 machine,
    however
     >     although the upgrade seems to be successfully, the existing
    RDP and
     >     SSH connections, don't longer work, the connection drops
    instantantly.
     >     Looking in the syslog, I see the following entry, which I
    think is
     >     the cause of the connections drops:
     >     /"/usr/local/sbin/guacd: symbol lookup error:
     >     /usr/local/lib/libguac.so.21: undefined symbol: FIPS_mode"/
     >
     >
     > This usually happens because some of the libraries from the previous
     > Guacamole version are left behind and then still get
    linked/referenced.
     > My suggestion would be;
     > * Remove all of the Guacamole binaries and libraries from the system.
     > * In the source directory, "make distclean" and then reconfigure,
     > rebuild, and install.
     > * Try the connections, again, and see if they work.
     >

    Just tried installing guacamole-server 1.5.2 on a fresh Ubuntu 22.04
    instance, and things appear to work correctly. I see no undefined
    symbol
    errors.

    The FIPS_mode() function is part of OpenSSL but is specific to OpenSSL
    1.x. It was deprecated and removed from OpenSSL 3.0, so the
    guacamole-server code uses that function only if built against an older
    OpenSSL:

    
https://github.com/apache/guacamole-server/blob/83ca7aa16b49830b5adb5a0ce60082b385163934/src/libguac/fips.c#L23-L45
 
<https://github.com/apache/guacamole-server/blob/83ca7aa16b49830b5adb5a0ce60082b385163934/src/libguac/fips.c#L23-L45>

    My guess would be that the version of OpenSSL present at build time was
    older, and that the version was upgraded later to a version that lacks
    FIPS_mode(). Rebuilding guacamole-server against the copy of OpenSSL
    currently present should solve the issue.

    - Mike

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