diff --git a/l10n_br_account_payment_brcobranca/constants/br_cobranca.py b/l10n_br_account_payment_brcobranca/constants/br_cobranca.py
index 2f061a5aee97..a320c1933e86 100644
--- a/l10n_br_account_payment_brcobranca/constants/br_cobranca.py
+++ b/l10n_br_account_payment_brcobranca/constants/br_cobranca.py
@@ -85,3 +85,20 @@ def get_brcobranca_api_url(env):
         )
 
     return brcobranca_api_url
+
+
+def handle_brcobranca_response(res):
+    if res.ok:
+        return True
+
+    error_msg = res.text
+    if "<html" in error_msg.lower():
+        error_msg = _(
+            "The BRCobranca service returned an HTML error page instead of the "
+            "expected response. This usually indicates a server-side crash, "
+            "a timeout, or a proxy configuration issue.\n\n"
+            "Status Code: %s",
+            res.status_code,
+        )
+
+    raise UserError(_("BRCobranca service error:\n%s") % error_msg)
diff --git a/l10n_br_account_payment_brcobranca/models/account_move.py b/l10n_br_account_payment_brcobranca/models/account_move.py
index ab4a44dc71b6..e40ac1acda3a 100644
--- a/l10n_br_account_payment_brcobranca/models/account_move.py
+++ b/l10n_br_account_payment_brcobranca/models/account_move.py
@@ -3,16 +3,20 @@
 # License AGPL-3.0 or later (http://www.gnu.org/licenses/agpl).
 
 import base64
+import io
 import json
 import logging
-import tempfile
 
 import requests
 
 from odoo import _, models
 from odoo.exceptions import UserError
 
-from ..constants.br_cobranca import TIMEOUT, get_brcobranca_api_url
+from ..constants.br_cobranca import (
+    TIMEOUT,
+    get_brcobranca_api_url,
+    handle_brcobranca_response,
+)
 
 logger = logging.getLogger(__name__)
 
@@ -59,10 +63,8 @@ def generate_boleto_pdf(self):
 
     def _get_brcobranca_boleto(self, boletos):
         content = json.dumps(boletos)
-        f = open(tempfile.mktemp(), "w")
-        f.write(content)
-        f.close()
-        files = {"data": open(f.name, "rb")}
+        data_file = io.BytesIO(content.encode("utf-8"))
+        files = {"data": ("boleto.json", data_file)}
 
         brcobranca_api_url = get_brcobranca_api_url(self.env)
         brcobranca_service_url = brcobranca_api_url + "/api/boleto/multi"
@@ -78,10 +80,8 @@ def _get_brcobranca_boleto(self, boletos):
             timeout=TIMEOUT,
         )
 
-        if str(res.status_code)[0] == "2":
-            pdf_string = res.content
-        else:
-            raise UserError(res.text.encode("utf-8"))
+        handle_brcobranca_response(res)
+        pdf_string = res.content
 
         return pdf_string
 
diff --git a/l10n_br_account_payment_brcobranca/models/account_move_line.py b/l10n_br_account_payment_brcobranca/models/account_move_line.py
index d06da2c3a4e6..1d73d906e8b4 100644
--- a/l10n_br_account_payment_brcobranca/models/account_move_line.py
+++ b/l10n_br_account_payment_brcobranca/models/account_move_line.py
@@ -25,6 +25,18 @@ class AccountMoveLine(models.Model):
     #  a ser usado sem a necessidade de criar um novo
     cnab_returned_ref = fields.Char(string="CNAB Returned Reference", copy=False)
 
+    def _get_brcobranca_address(self, partner):
+        address_parts = [
+            f"{partner.street_name or ''} {partner.street_number or ''}".strip(),
+            partner.district,
+            partner.city_id.name,
+            partner.state_id.code,
+        ]
+        address = ", ".join(filter(None, address_parts))
+        if partner.zip:
+            address += f" CEP:{partner.zip}"
+        return address[:100]  # Standard limit for many banks
+
     # see the list of brcobranca boleto fields:
     # https://github.com/kivanio/brcobranca/blob/master/lib/
     # brcobranca/boleto/base.rb
@@ -49,17 +61,9 @@ def send_payment(self):
                 "bank": bank_name_brcobranca[0],
                 "valor": str("%.2f" % move_line.debit),
                 "cedente": move_line.company_id.partner_id.legal_name,
-                "cedente_endereco": (move_line.company_id.partner_id.street_name or "")
-                + " "
-                + (move_line.company_id.partner_id.street_number or "")
-                + ", "
-                + (move_line.company_id.partner_id.district or "")
-                + ", "
-                + (move_line.company_id.partner_id.city_id.name or "")
-                + " - "
-                + (move_line.company_id.partner_id.state_id.code or "")
-                + " "
-                + ("CEP:" + move_line.company_id.partner_id.zip or ""),
+                "cedente_endereco": self._get_brcobranca_address(
+                    move_line.company_id.partner_id
+                ),
                 "documento_cedente": move_line.company_id.cnpj_cpf,
                 "sacado": move_line.partner_id.legal_name,
                 "sacado_documento": move_line.partner_id.cnpj_cpf,
@@ -79,17 +83,7 @@ def send_payment(self):
                 ),
                 "moeda": DICT_BRCOBRANCA_CURRENCY["R$"],
                 "aceite": cnab_config.boleto_accept,
-                "sacado_endereco": (move_line.partner_id.street_name or "")
-                + " "
-                + (move_line.partner_id.street_number or "")
-                + ", "
-                + (move_line.partner_id.district or "")
-                + ", "
-                + (move_line.partner_id.city_id.name or "")
-                + " - "
-                + (move_line.partner_id.state_id.code or "")
-                + " "
-                + ("CEP:" + move_line.partner_id.zip or ""),
+                "sacado_endereco": self._get_brcobranca_address(move_line.partner_id),
                 "data_processamento": move_line.move_id.invoice_date.strftime(
                     "%Y/%m/%d"
                 ),
diff --git a/l10n_br_account_payment_brcobranca/models/account_payment_order.py b/l10n_br_account_payment_brcobranca/models/account_payment_order.py
index 5a8060f3e82b..9e7b23fcf8bb 100644
--- a/l10n_br_account_payment_brcobranca/models/account_payment_order.py
+++ b/l10n_br_account_payment_brcobranca/models/account_payment_order.py
@@ -4,9 +4,9 @@
 # @author Luis Felipe Mileo <mileo@kmee.com.br>
 # License AGPL-3.0 or later (http://www.gnu.org/licenses/agpl).
 
+import io
 import json
 import logging
-import tempfile
 
 import requests
 from erpbrasil.base import misc
@@ -19,6 +19,7 @@
     TIMEOUT,
     get_brcobranca_api_url,
     get_brcobranca_bank,
+    handle_brcobranca_response,
 )
 
 _logger = logging.getLogger(__name__)
@@ -171,10 +172,8 @@ def generate_payment_file(self):
 
     def _get_brcobranca_remessa(self, bank_brcobranca, remessa_values, cnab_type):
         content = json.dumps(remessa_values)
-        f = open(tempfile.mktemp(), "w")
-        f.write(content)
-        f.close()
-        files = {"data": open(f.name, "rb")}
+        data_file = io.BytesIO(content.encode("utf-8"))
+        files = {"data": ("remessa.json", data_file)}
 
         brcobranca_api_url = get_brcobranca_api_url(self.env)
         # EX.: "http://boleto_cnab_api:9292/api/remessa"
@@ -194,6 +193,8 @@ def _get_brcobranca_remessa(self, bank_brcobranca, remessa_values, cnab_type):
             timeout=TIMEOUT,
         )
 
+        handle_brcobranca_response(res)
+
         if cnab_type == "240" and "R01" in res.text[242:254]:
             #  Todos os header de lote cnab 240 tem conteúdo: R01,
             #  verificar observações G025 e G028 do manual cnab 240 febraban.
@@ -206,7 +207,14 @@ def _get_brcobranca_remessa(self, bank_brcobranca, remessa_values, cnab_type):
             # https://github.com/kivanio/brcobranca/tree/master/spec/fixtures/remessa
             remessa = res.content
         else:
-            raise ValidationError(res.text)
+            raise ValidationError(
+                _(
+                    "The BRCobranca service returned a success status, but the "
+                    "content of the generated CNAB file is invalid or unexpected.\n\n"
+                    "Response content: %s",
+                    res.text[:500],
+                )
+            )
 
         return remessa
 
diff --git a/l10n_br_account_payment_brcobranca/parser/cnab_file_parser.py b/l10n_br_account_payment_brcobranca/parser/cnab_file_parser.py
index f3913c0c3aa1..8932a5c426ee 100644
--- a/l10n_br_account_payment_brcobranca/parser/cnab_file_parser.py
+++ b/l10n_br_account_payment_brcobranca/parser/cnab_file_parser.py
@@ -9,11 +9,13 @@
 
 import requests
 
-from odoo.exceptions import UserError
-
 from odoo.addons.account_move_base_import.parser.file_parser import FileParser
 
-from ..constants.br_cobranca import TIMEOUT, get_brcobranca_api_url
+from ..constants.br_cobranca import (
+    TIMEOUT,
+    get_brcobranca_api_url,
+    handle_brcobranca_response,
+)
 
 logger = logging.getLogger(__name__)
 
@@ -94,8 +96,7 @@ def _get_brcobranca_retorno(self, files):
             timeout=TIMEOUT,
         )
 
-        if res.status_code != 201:
-            raise UserError(res.text)
+        handle_brcobranca_response(res)
 
         string_result = res.json()
         data = json.loads(string_result)
@@ -239,7 +240,10 @@ def process_return_file(self, data):
                     {
                         "occurrences": descricao_ocorrencia,
                         "occurrence_date": data_ocorrencia,
-                        "str_motiv_a": " * - BOLETO NÃO ENCONTRADO.",
+                        "str_motiv_a": (
+                            f" * - BOLETO NÃO ENCONTRADO para o "
+                            f"Nosso Número {linha_cnab['nosso_numero']}."
+                        ),
                         "own_number": linha_cnab["nosso_numero"],
                         "your_number": linha_cnab["documento_numero"],
                         "title_value": valor_titulo,