Error PathTooLongException

I run letsencrypt program on Windows Server 2008 R2 with IIS 7.5. I try to generate a SAN certificate for all bindings of multiple IIS sites but I receive this error PathTooLongException. If I reduce the number of sites, the program generates and installs correctly the new certificate. But I need to generate a certificate for all web sites installed (85 domain name). Can i solve this problem. Thanks

I moved this to "Help" as a more accurate topic. Normally you're provided with a list of questions when opening a topic under Help originally. Could you please fill out the following? There are dozens of Let's Encrypt clients you could be using, and even more different ways you could be going about attempting to use these clients, so we really do need more information to help.

Please fill out the fields below so we can help you better. Note: you must provide your domain name to get help. Domain names for issued certificates are all made public in Certificate Transparency logs (e.g. crt.sh | example.com), so withholding your domain name here does not increase secrecy, but only makes it harder for us to provide help.

My domain is:

I ran this command:

It produced this output:

My web server is (include version):

The operating system my web server runs on is (include version):

My hosting provider, if applicable, is:

I can login to a root shell on my machine (yes or no, or I don't know):

I'm using a control panel to manage my site (no, or provide the name and version of the control panel):

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My domain is:
www.emilianaparati.com
www.villaiciabattini.it
download.trienergia.it
www.agrisystemdicipriani.it
www.adiwallcoverings.it
www.decoriwallcoverings.it
www.esedrawallcoverings.it
ferre.emilianaparati.com
www.tekkowallcoverings.it
yudashkin.emilianaparati.it
ordini.emilianaparati.com
www.epwallcoverings.it
www.villaspinosa.it
agriturismo.villaspinosa.it
cultura.villaspinosa.it
events.villaspinosa.com
www.villaspinosa.com
holidays.villaspinosa.com
matrimoni.villaspinosa.it
vini.villaspinosa.it
enoteca.villaspinosa.it
winetasting.villaspinosa.com
weddings.villaspinosa.com
wines.villaspinosa.com
www.globalprivacy.it
globalprivacy.it
www.argentiera.eu
crm.fiorenzofratini.com
www.associazionefiorenzofratini.com
www.palazzotornabuoni.com
www.cosmopro.eu
www.3tsrl.com
www.airtopitalia.com
agenti.alimentis.it
www.ate-srl.com
www.barriquenet.it
www.beveragenet.it
www.brigaldara.it
www.brungelmino.it
www.comarsport.com


www.kw-suspensions.it
www.dalfior.com
www.caterinazangrando.com
www.lameplastgroup.com
www.ravelsrl.it
www.rivacostruzioni.com
www.rock-planet.it
www.cashdesknet.it
www.castelmerlino.com
www.ciclisticacavriago.it
restricted.comitatoimi.it
www.ddl.re.it
www.fratellidichiara.it
www.centroserviziaz.it
www.fiordimelone.com
www.formephysique.it
www.gandolfisrl.it
www.hobbypescaeacquari.com
www.ideapcweb.com
www.imperial-fishing.it
portale.info-res.it
www.ivishock.it
www.music.lievitomadre.it
www.lisolante.it
www.medicinameccanica.it
www.mellonigomma.com
catalogo.mossini.it
www.nataleperlemilia.it
www.tecno-tre.it
www.newlifeinvela.it
portale.grappanonino.it
nuotoclub.sesamopiscine.it
www.printthebestsavetherest.it
www.sesamopiscine.it
www.stallapiazzola.it
www.studiomosconi.it
www.terraferma-emilia.it
solleciti.uniontrade.it
documenti.uniontrade.it

I ran this command: C:\letsencript\letsencrypt

[INFO] Let’s Encrypt Windows Simple (LEWS)
[INFO] Software version 198.2.6594.21512 (RELEASE)
[INFO] IIS version 7.5
[INFO] ACME Server https://acme-v01.api.letsencrypt.org/
[INFO] Please report issues at https://github.com/Lone-Coder/letsencrypt-win-simple

N: Create new certificate
3: SAN certificate for all bindings of multiple IIS sites

List of ID: 59,19,117,40,100,60,64,61,62,66,55,63,192,188,186,187,193,189,182,190,184,185,183,191,37,65,106,148,71,28,41,175,75,130,94,95,54,120,84,69,146,156,53,56,151,77,17,103,23,49,84,47,118,179,32,116,128,31,70,83,6,76,160,146,21,92,29,127,79,80,27,180,140,174,124,51,93,20,33,144

None escluded

It produced this output:

[INFO] Plugin IISSites generated target [IISSites] 59,19,117,40,100,60,64,61,62
,66,55,63,192,188,186,187,193,189,182,190,184,185,183,191,37,65,106,148,71,28,41
,175,75,130,94,95,54,120,84,69,146,156,53,56,151,77,17,103,23,49,47,118,179,32,1
16,128,31,70,83,6,76,160,21,92,29,127,79,80,27,180,140,174,124,51,93,20,33,144 (
SiteId -1) [81 bindings - www.emilianaparati.com, … @ x]
[EROR] PathTooLongException: Percorso e/o nome di file specificato troppo lungo. Il nome di file completo deve contenere meno di 260 caratteri, mentre il nome di directory deve contenere meno di 248 caratteri.
[EROR] Create certificate failed

My web server is (include version): IIS 7.5

The operating system my web server runs on is (include version): Windows Server 2008 R2 - Service Pack 1

My hosting provider, if applicable, is:

I can login to a root shell on my machine (yes or no, or I don’t know): yes

I’m using a control panel to manage my site (no, or provide the name and version of the control panel): IIS Control Panel

Thank you

Ok, so I’m not very familiar with the Lets-Encrypt-Win-Simple client (it seems to have been abandoned as well, last update was over two years ago), but I don’t believe that error should be the result of having too many domains listed. I believe the issue is that your web root paths may be too long. Windows can’t handle filenames greater than 260 characters. Since Let’s Encrypt challenge file names are around 44 characters long already, that leaves 216 characters for the rest of the filename. Given that they are placed under the web root in /.well-known/acme-challenge/ that takes you down to around 188 characters. Are these websites hosted out of particularly long directories?

My directories have 15/20 characters (60/70 with full path). I see that letsencrypt generate a certificate with a name very long. It has the list of id as name. I attached a print screen… Could it be that the problem? Can I customize the certificate name from a parameter?

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