diff --git a/docker/py-ews/Dockerfile b/docker/py-ews/Dockerfile
index 4a71ffe04bbc8..aebe468b043f5 100644
--- a/docker/py-ews/Dockerfile
+++ b/docker/py-ews/Dockerfile
@@ -1,7 +1,6 @@
+# Last modified: 2025-09-12T03:11:14.185937+00:00
 
-FROM demisto/python3-deb:3.12.7.117935
-
-# END Docker file from https://raw.githubusercontent.com/docker-library/python/331890ef059fae05f84c652520b78c340526dc71/3.10/bullseye/Dockerfile
+FROM demisto/python3-deb:3.12.11.4801753
 
 # Basic linux utilities
 RUN apt-get update && apt-get install -y --no-install-recommends \
@@ -12,35 +11,28 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 RUN apt-get update && apt-get -y --no-install-recommends upgrade \
 && rm -rf /var/lib/apt/lists/*
 
-#RUN rm CVE-2021-3177.diff
 COPY requirements.txt .
 
-#Install tools for building binary deps (will be reomved later on)
-RUN apt-get update && apt-get install -y -f --no-install-recommends --allow-downgrades \
+# Install runtime libraries first
+RUN apt-get update && apt-get install -y --no-install-recommends \
+    libxml2 \
+    libxslt1.1 \
+&& rm -rf /var/lib/apt/lists/*
+
+# Install build dependencies, build packages, then remove build deps
+RUN apt-get update && apt-get install -y --no-install-recommends \
     gcc \
-    libcom-err2=1.46.2-2+deb11u1 \
     python3-dev \
     build-essential \
-    wget \
-    git \
-    libxml2 \
-    libxslt1.1 \
-	libkrb5-3 \
-    libffi-dev \
     libxml2-dev \
     libxslt-dev \
     libssl-dev \
-    libkrb5-dev \
 && pip install --no-cache-dir -r requirements.txt \
 && apt-get purge -y --auto-remove \
-  gcc \
-  python3-dev \
-  build-essential \
-  git \
-  wget \
-  libffi-dev \
-  wget \
-  libxml2-dev \
-  libssl-dev \
-  libkrb5-dev \
+    gcc \
+    python3-dev \
+    build-essential \
+    libxml2-dev \
+    libxslt-dev \
+    libssl-dev \
 && rm -rf /var/lib/apt/lists/*
diff --git a/docker/py-ews/Pipfile b/docker/py-ews/Pipfile
index 59cc5b8ede62c..e73adc26268d7 100644
--- a/docker/py-ews/Pipfile
+++ b/docker/py-ews/Pipfile
@@ -7,33 +7,9 @@ verify_ssl = true
 
 [packages]
 exchangelib = ">=5.4.1"
-chardet = "*"
 dateparser = "*"
-asn1crypto = "*"
-cached-property = "*"
-certifi = "*"
-cffi = "*"
-cryptography = "*"
-defusedxml = "*"
-dnspython = "*"
-enum34 = "*"
-future = "*"
-idna = "*"
-ipaddress = "*"
-isodate = "*"
 lxml = "*"
-ntlm-auth = "*"
-pycparser = "*"
-pygments = "*"
-pykerberos = "*"
-python-dateutil = "*"
-pytz = "*"
-requests = ">=2.32.3"
-requests-kerberos = "*"
 requests-ntlm = "==1.1.0" # lock because of https://github.com/requests/requests-ntlm/issues/136
-six = "*"
-tzlocal = "*"
-urllib3 = "<2"
 
 [requires]
 python_version = "3.12"
\ No newline at end of file
diff --git a/docker/py-ews/Pipfile.lock b/docker/py-ews/Pipfile.lock
index d15d50c505810..ed55c9f71d004 100644
--- a/docker/py-ews/Pipfile.lock
+++ b/docker/py-ews/Pipfile.lock
@@ -1,7 +1,7 @@
 {
     "_meta": {
         "hash": {
-            "sha256": "928caec54efdc15328040a1cf20428ace80c3214099375466c7a43674505ffc5"
+            "sha256": "d2f8fc78e7d308d3b4c7ca0c9ace9aff3f2a1b4b319ae4728a74eb4de27a3f86"
         },
         "pipfile-spec": 6,
         "requires": {
@@ -16,732 +16,560 @@
         ]
     },
     "default": {
-        "asn1crypto": {
-            "hashes": [
-                "sha256:13ae38502be632115abf8a24cbe5f4da52e3b5231990aff31123c805306ccb9c",
-                "sha256:db4e40728b728508912cbb3d44f19ce188f218e9eba635821bb4b68564f8fd67"
-            ],
-            "index": "pypi",
-            "version": "==1.5.1"
-        },
         "cached-property": {
             "hashes": [
                 "sha256:484d617105e3ee0e4f1f58725e72a8ef9e93deee462222dbd51cd91230897641",
                 "sha256:f617d70ab1100b7bcf6e42228f9ddcb78c676ffa167278d9f730d1c2fba69ccb"
             ],
-            "index": "pypi",
             "markers": "python_version >= '3.8'",
             "version": "==2.0.1"
         },
         "certifi": {
             "hashes": [
-                "sha256:922820b53db7a7257ffbda3f597266d435245903d80737e34f8a45ff3e3230d8",
-                "sha256:bec941d2aa8195e248a60b31ff9f0558284cf01a52591ceda73ea9afffd69fd9"
+                "sha256:e564105f78ded564e3ae7c923924435e1daa7463faeab5bb932bc53ffae63407",
+                "sha256:f6c12493cfb1b06ba2ff328595af9350c65d6644968e5d3a2ffd78699af217a5"
             ],
-            "index": "pypi",
-            "markers": "python_version >= '3.6'",
-            "version": "==2024.8.30"
+            "markers": "python_version >= '3.7'",
+            "version": "==2025.8.3"
         },
         "cffi": {
             "hashes": [
-                "sha256:045d61c734659cc045141be4bae381a41d89b741f795af1dd018bfb532fd0df8",
-                "sha256:0984a4925a435b1da406122d4d7968dd861c1385afe3b45ba82b750f229811e2",
-                "sha256:0e2b1fac190ae3ebfe37b979cc1ce69c81f4e4fe5746bb401dca63a9062cdaf1",
-                "sha256:0f048dcf80db46f0098ccac01132761580d28e28bc0f78ae0d58048063317e15",
-                "sha256:1257bdabf294dceb59f5e70c64a3e2f462c30c7ad68092d01bbbfb1c16b1ba36",
-                "sha256:1c39c6016c32bc48dd54561950ebd6836e1670f2ae46128f67cf49e789c52824",
-                "sha256:1d599671f396c4723d016dbddb72fe8e0397082b0a77a4fab8028923bec050e8",
-                "sha256:28b16024becceed8c6dfbc75629e27788d8a3f9030691a1dbf9821a128b22c36",
-                "sha256:2bb1a08b8008b281856e5971307cc386a8e9c5b625ac297e853d36da6efe9c17",
-                "sha256:30c5e0cb5ae493c04c8b42916e52ca38079f1b235c2f8ae5f4527b963c401caf",
-                "sha256:31000ec67d4221a71bd3f67df918b1f88f676f1c3b535a7eb473255fdc0b83fc",
-                "sha256:386c8bf53c502fff58903061338ce4f4950cbdcb23e2902d86c0f722b786bbe3",
-                "sha256:3edc8d958eb099c634dace3c7e16560ae474aa3803a5df240542b305d14e14ed",
-                "sha256:45398b671ac6d70e67da8e4224a065cec6a93541bb7aebe1b198a61b58c7b702",
-                "sha256:46bf43160c1a35f7ec506d254e5c890f3c03648a4dbac12d624e4490a7046cd1",
-                "sha256:4ceb10419a9adf4460ea14cfd6bc43d08701f0835e979bf821052f1805850fe8",
-                "sha256:51392eae71afec0d0c8fb1a53b204dbb3bcabcb3c9b807eedf3e1e6ccf2de903",
-                "sha256:5da5719280082ac6bd9aa7becb3938dc9f9cbd57fac7d2871717b1feb0902ab6",
-                "sha256:610faea79c43e44c71e1ec53a554553fa22321b65fae24889706c0a84d4ad86d",
-                "sha256:636062ea65bd0195bc012fea9321aca499c0504409f413dc88af450b57ffd03b",
-                "sha256:6883e737d7d9e4899a8a695e00ec36bd4e5e4f18fabe0aca0efe0a4b44cdb13e",
-                "sha256:6b8b4a92e1c65048ff98cfe1f735ef8f1ceb72e3d5f0c25fdb12087a23da22be",
-                "sha256:6f17be4345073b0a7b8ea599688f692ac3ef23ce28e5df79c04de519dbc4912c",
-                "sha256:706510fe141c86a69c8ddc029c7910003a17353970cff3b904ff0686a5927683",
-                "sha256:72e72408cad3d5419375fc87d289076ee319835bdfa2caad331e377589aebba9",
-                "sha256:733e99bc2df47476e3848417c5a4540522f234dfd4ef3ab7fafdf555b082ec0c",
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-                "sha256:b62ce867176a75d03a665bad002af8e6d54644fad99a3c70905c543130e39d93",
-                "sha256:c03e868a0b3bc35839ba98e74211ed2b05d2119be4e8a0f224fba9384f1fe02e",
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-                "sha256:c9c3d058ebabb74db66e431095118094d06abf53284d9c81f27300d0e0d8bc7c",
-                "sha256:ca74b8dbe6e8e8263c0ffd60277de77dcee6c837a3d0881d8c1ead7268c9e576",
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-                "sha256:da95af8214998d77a98cc14e3a3bd00aa191526343078b530ceb0bd710fb48a5",
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-                "sha256:df8b1c11f177bc2313ec4b2d46baec87a5f3e71fc8b45dab2ee7cae86d9aba14",
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-                "sha256:fc48c783f9c87e60831201f2cce7f3b2e4846bf4d8728eabe54d60700b318a0b"
+                "sha256:00bdf7acc5f795150faa6957054fbbca2439db2f775ce831222b66f192f03beb",
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+                "sha256:0cf2d91ecc3fcc0625c2c530fe004f82c110405f101548512cce44322fa8ac44",
+                "sha256:0f6084a0ea23d05d20c3edcda20c3d006f9b6f3fefeac38f59262e10cef47ee2",
+                "sha256:12873ca6cb9b0f0d3a0da705d6086fe911591737a59f28b7936bdfed27c0d47c",
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+                "sha256:1cd13c99ce269b3ed80b417dcd591415d3372bcac067009b6e0f59c7d4015e65",
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+                "sha256:b4c854ef3adc177950a8dfc81a86f5115d2abd545751a304c5bcf2c2c7283cfe",
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@@ -761,38 +589,35 @@
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             "hashes": [
-                "sha256:1e61c37477a1626458e36f7b1d82aa5c9b094fa4802892072e49de9c60c4c926",
-                "sha256:8abb2f1d86890a2dfb989f9a77cfcfd3e47c2a354b01111771326f8aa26e0254"
+                "sha256:4721f391ed90541fddacab5acf947aa0d3dc7d27b2e1e8eda2be8970586c3274",
+                "sha256:ff70335d468e7eb6ec65b95b99d3a2836546063f63acc5171de367e834932a81"
             ],
-            "index": "pypi",
             "markers": "python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2'",
-            "version": "==1.16.0"
+            "version": "==1.17.0"
         },
         "tzdata": {
             "hashes": [
-                "sha256:7d85cc416e9382e69095b7bdf4afd9e3880418a2413feec7069d533d6b4e31cc",
-                "sha256:a48093786cdcde33cad18c2555e8532f34422074448fbc874186f0abd79565cd"
+                "sha256:1a403fada01ff9221ca8044d701868fa132215d84beb92242d9acd2147f667a8",
+                "sha256:b60a638fcc0daffadf82fe0f57e53d06bdec2f36c4df66280ae79bce6bd6f2b9"
             ],
             "markers": "python_version >= '2'",
-            "version": "==2024.2"
+            "version": "==2025.2"
         },
         "tzlocal": {
             "hashes": [
-                "sha256:49816ef2fe65ea8ac19d19aa7a1ae0551c834303d5014c6d5a62e4cbda8047b8",
-                "sha256:8d399205578f1a9342816409cc1e46a93ebd5755e39ea2d85334bea911bf0e6e"
+                "sha256:cceffc7edecefea1f595541dbd6e990cb1ea3d19bf01b2809f362a03dd7921fd",
+                "sha256:eb1a66c3ef5847adf7a834f1be0800581b683b5608e74f86ecbcef8ab91bb85d"
             ],
-            "index": "pypi",
-            "markers": "python_version >= '3.8'",
-            "version": "==5.2"
+            "markers": "python_version >= '3.9'",
+            "version": "==5.3.1"
         },
         "urllib3": {
             "hashes": [
-                "sha256:0ed14ccfbf1c30a9072c7ca157e4319b70d65f623e91e7b32fadb2853431016e",
-                "sha256:40c2dc0c681e47eb8f90e7e27bf6ff7df2e677421fd46756da1161c39ca70d32"
+                "sha256:3fc47733c7e419d4bc3f6b3dc2b4f890bb743906a30d56ba4a5bfa4bbff92760",
+                "sha256:e6b01673c0fa6a13e374b50871808eb3bf7046c4b125b216f6bf1cc604cff0dc"
             ],
-            "index": "pypi",
-            "markers": "python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3, 3.4, 3.5'",
-            "version": "==1.26.20"
+            "markers": "python_version >= '3.9'",
+            "version": "==2.5.0"
         }
     },
     "develop": {}
diff --git a/docker/py-ews/verify.py b/docker/py-ews/verify.py
index 4dc49bfa9372b..d8674c0c2c5d0 100644
--- a/docker/py-ews/verify.py
+++ b/docker/py-ews/verify.py
@@ -1,37 +1,52 @@
 import email
 import hashlib
-import subprocess
-import warnings
-from collections import deque
+from email.policy import SMTP, SMTPUTF8
+from io import StringIO
 from multiprocessing import Process
 
-import lxml
 import dateparser
-import exchangelib
-from io import StringIO
-from exchangelib import (BASIC, DELEGATE, DIGEST, IMPERSONATION, NTLM, Account,
-                         Body, Build, Configuration, Credentials, EWSDateTime,
-                         EWSTimeZone, FileAttachment, Folder, HTMLBody,
-                         ItemAttachment, Version)
-from exchangelib.errors import (AutoDiscoverFailed, ErrorFolderNotFound,
-                                ErrorInvalidIdMalformed,
-                                ErrorInvalidPropertyRequest,
-                                ErrorIrresolvableConflict, ErrorItemNotFound,
-                                ErrorMailboxMoveInProgress,
-                                ErrorMailboxStoreUnavailable,
-                                ErrorNameResolutionNoResults, RateLimitError,
-                                ResponseMessageError, TransportError)
+from exchangelib import (
+    BASIC,
+    DELEGATE,
+    DIGEST,
+    IMPERSONATION,
+    NTLM,
+    Body,
+    EWSDateTime,
+    EWSTimeZone,
+    FileAttachment,
+    FolderCollection,
+    HTMLBody,
+    ItemAttachment,
+    Version,
+)
+from exchangelib.errors import (
+    ErrorCannotOpenFileAttachment,
+    ErrorFolderNotFound,
+    ErrorInvalidPropertyRequest,
+    ErrorIrresolvableConflict,
+    ErrorMailboxMoveInProgress,
+    ErrorMailboxStoreUnavailable,
+    ErrorMimeContentConversionFailed,
+    ErrorNameResolutionNoResults,
+    RateLimitError,
+    TransportError,
+)
 from exchangelib.items import Contact, Item, Message
-from exchangelib.protocol import BaseProtocol, Protocol
 from exchangelib.services import EWSService
-from exchangelib.services.common import EWSAccountService
 from exchangelib.util import add_xml_child, create_element
-from exchangelib.version import (EXCHANGE_2007, EXCHANGE_2010,
-                                 EXCHANGE_2010_SP2, EXCHANGE_2013,
-                                 EXCHANGE_2016, EXCHANGE_2019)
-from future import utils as future_utils
+from exchangelib.version import (
+    EXCHANGE_2007,
+    EXCHANGE_2010,
+    EXCHANGE_2010_SP2,
+    EXCHANGE_2013,
+    EXCHANGE_2013_SP1,
+    EXCHANGE_2016,
+    EXCHANGE_2019,
+)
+from exchangelib.version import VERSIONS as EXC_VERSIONS
 from requests.exceptions import ConnectionError
-from _sqlite3 import *
+
 # verify that we support dh 1024
 import requests
 requests.packages.urllib3.util.ssl_.DEFAULT_CIPHERS ='@SECLEVEL=1:ECDHE+AESGCM:ECDHE+CHACHA20:DHE+AESGCM:DHE+CHACHA20:ECDH+AESGCM:DH+AESGCM:' \