diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index 46c86103ad..753c1ac28b 100644
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -42,3 +42,23 @@ post:
   - func: "upload mo artifacts"
   - func: "upload test results"
   - func: "cleanup"
+
+tasks:
+  - name: resync_specs
+    commands:
+      - command: subprocess.exec
+        params:
+          binary: bash
+          include_expansions_in_env: [AWS_ACCESS_KEY_ID, AWS_SECRET_ACCESS_KEY, AWS_SESSION_TOKEN]
+          args:
+            - .evergreen/scripts/resync-all-specs.sh
+          working_dir: src
+
+buildvariants:
+  - name: resync_specs
+    display_name: "Resync Specs"
+    run_on: rhel80-small
+    cron: '0 16 * * MON'
+    patchable: false
+    tasks:
+      - name: resync_specs
diff --git a/.evergreen/patch/PYTHON-4884.patch b/.evergreen/patch/PYTHON-4884.patch
new file mode 100644
index 0000000000..0ef66e072a
--- /dev/null
+++ b/.evergreen/patch/PYTHON-4884.patch
@@ -0,0 +1,12 @@
+diff --git a/test/bson_corpus/datetime.json b/test/bson_corpus/datetime.json
+index f857afdc..1554341d 100644
+--- a/test/bson_corpus/datetime.json
++++ b/test/bson_corpus/datetime.json
+@@ -24,6 +24,7 @@
+         {
+             "description" : "Y10K",
+             "canonical_bson" : "1000000009610000DC1FD277E6000000",
++            "relaxed_extjson" : "{\"a\":{\"$date\":{\"$numberLong\":\"253402300800000\"}}}",
+             "canonical_extjson" : "{\"a\":{\"$date\":{\"$numberLong\":\"253402300800000\"}}}"
+         },
+         {
diff --git a/.evergreen/patch/PYTHON-4918.patch b/.evergreen/patch/PYTHON-4918.patch
new file mode 100644
index 0000000000..5f409c5870
--- /dev/null
+++ b/.evergreen/patch/PYTHON-4918.patch
@@ -0,0 +1,24 @@
+diff --git a/test/connection_monitoring/pool-create-min-size-error.json b/test/connection_monitoring/pool-create-min-size-error.json
+index 1c744b85..509b2a23 100644
+--- a/test/connection_monitoring/pool-create-min-size-error.json
++++ b/test/connection_monitoring/pool-create-min-size-error.json
+@@ -49,15 +49,15 @@
+       "type": "ConnectionCreated",
+       "address": 42
+     },
++    {
++      "type": "ConnectionPoolCleared",
++      "address": 42
++    },
+     {
+       "type": "ConnectionClosed",
+       "address": 42,
+       "connectionId": 42,
+       "reason": "error"
+-    },
+-    {
+-      "type": "ConnectionPoolCleared",
+-      "address": 42
+     }
+   ],
+   "ignore": [
diff --git a/.evergreen/patch/PYTHON-4931.patch b/.evergreen/patch/PYTHON-4931.patch
new file mode 100644
index 0000000000..ad7086b378
--- /dev/null
+++ b/.evergreen/patch/PYTHON-4931.patch
@@ -0,0 +1,93 @@
+diff --git a/test/gridfs/delete.json b/test/gridfs/delete.json
+index 277b9ed7..9a9b22fc 100644
+--- a/test/gridfs/delete.json
++++ b/test/gridfs/delete.json
+@@ -497,7 +497,7 @@
+             }
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ],
+@@ -650,7 +650,7 @@
+             }
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ],
+diff --git a/test/gridfs/download.json b/test/gridfs/download.json
+index f0cb8517..67658ac5 100644
+--- a/test/gridfs/download.json
++++ b/test/gridfs/download.json
+@@ -338,7 +338,7 @@
+             }
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ]
+@@ -370,7 +370,7 @@
+             }
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ]
+@@ -402,7 +402,7 @@
+             }
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ]
+@@ -471,7 +471,7 @@
+             }
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ]
+@@ -514,7 +514,7 @@
+             }
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ]
+diff --git a/test/gridfs/downloadByName.json b/test/gridfs/downloadByName.json
+index 7b20933c..45abaf7b 100644
+--- a/test/gridfs/downloadByName.json
++++ b/test/gridfs/downloadByName.json
+@@ -290,7 +290,7 @@
+             "filename": "xyz"
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ]
+@@ -306,7 +306,7 @@
+             "revision": 999
+           },
+           "expectError": {
+-            "isError": true
++            "isClientError": true
+           }
+         }
+       ]
diff --git a/.evergreen/patch/PYTHON-5237.patch b/.evergreen/patch/PYTHON-5237.patch
new file mode 100644
index 0000000000..01de56b6c8
--- /dev/null
+++ b/.evergreen/patch/PYTHON-5237.patch
@@ -0,0 +1,48 @@
+diff --git a/test/sessions/driver-sessions-dirty-session-errors.json b/test/sessions/driver-sessions-dirty-session-errors.json
+index 6aa1da1d..d7a1c6ab 100644
+--- a/test/sessions/driver-sessions-dirty-session-errors.json
++++ b/test/sessions/driver-sessions-dirty-session-errors.json
+@@ -347,7 +347,9 @@
+                       "x": 1
+                     }
+                   },
+-                  "new": false,
++                  "new": {
++                    "$$unsetOrMatches": false
++                  },
+                   "lsid": {
+                     "$$sessionLsid": "session0"
+                   },
+@@ -375,7 +377,9 @@
+                       "x": 1
+                     }
+                   },
+-                  "new": false,
++                  "new": {
++                    "$$unsetOrMatches": false
++                  },
+                   "lsid": {
+                     "$$sessionLsid": "session0"
+                   },
+@@ -627,7 +631,9 @@
+                       "x": 1
+                     }
+                   },
+-                  "new": false,
++                  "new": {
++                    "$$unsetOrMatches": false
++                  },
+                   "lsid": {
+                     "$$type": "object"
+                   },
+@@ -655,7 +661,9 @@
+                       "x": 1
+                     }
+                   },
+-                  "new": false,
++                  "new": {
++                    "$$unsetOrMatches": false
++                  },
+                   "lsid": {
+                     "$$type": "object"
+                   },
diff --git a/.evergreen/remove-unimplemented-tests.sh b/.evergreen/remove-unimplemented-tests.sh
new file mode 100755
index 0000000000..8c5414891e
--- /dev/null
+++ b/.evergreen/remove-unimplemented-tests.sh
@@ -0,0 +1,46 @@
+#!/bin/bash
+PYMONGO=$(dirname "$(cd "$(dirname "$0")" || exit; pwd)")
+
+rm -rf $PYMONGO/test/server_selection/logging
+rm $PYMONGO/test/transactions/legacy/errors-client.json  # PYTHON-1894
+rm $PYMONGO/test/connection_monitoring/wait-queue-fairness.json  # PYTHON-1873
+rm $PYMONGO/test/client-side-encryption/spec/unified/fle2v2-BypassQueryAnalysis.json  # PYTHON-5143
+rm $PYMONGO/test/client-side-encryption/spec/unified/fle2v2-EncryptedFields-vs-EncryptedFieldsMap.json  # PYTHON-5143
+rm $PYMONGO/test/client-side-encryption/spec/unified/localSchema.json  # PYTHON-5143
+rm $PYMONGO/test/client-side-encryption/spec/unified/maxWireVersion.json  # PYTHON-5143
+rm $PYMONGO/test/unified-test-format/valid-pass/poc-queryable-encryption.json  # PYTHON-5143
+rm $PYMONGO/test/gridfs/rename.json  # PYTHON-4931
+rm $PYMONGO/test/discovery_and_monitoring/unified/pool-clear-application-error.json  # PYTHON-4918
+rm $PYMONGO/test/discovery_and_monitoring/unified/pool-clear-checkout-error.json  # PYTHON-4918
+rm $PYMONGO/test/discovery_and_monitoring/unified/pool-clear-min-pool-size-error.json  # PYTHON-4918
+
+# Python doesn't implement DRIVERS-3064
+rm $PYMONGO/test/collection_management/listCollections-rawdata.json
+rm $PYMONGO/test/crud/unified/aggregate-rawdata.json
+rm $PYMONGO/test/crud/unified/bulkWrite-deleteMany-rawdata.json
+rm $PYMONGO/test/crud/unified/bulkWrite-deleteOne-rawdata.json
+rm $PYMONGO/test/crud/unified/bulkWrite-replaceOne-rawdata.json
+rm $PYMONGO/test/crud/unified/bulkWrite-updateMany-rawdata.json
+rm $PYMONGO/test/crud/unified/bulkWrite-updateOne-rawdata.json
+rm $PYMONGO/test/crud/unified/client-bulkWrite-delete-rawdata.json
+rm $PYMONGO/test/crud/unified/client-bulkWrite-replaceOne-rawdata.json
+rm $PYMONGO/test/crud/unified/client-bulkWrite-update-rawdata.json
+rm $PYMONGO/test/crud/unified/count-rawdata.json
+rm $PYMONGO/test/crud/unified/countDocuments-rawdata.json
+rm $PYMONGO/test/crud/unified/db-aggregate-rawdata.json
+rm $PYMONGO/test/crud/unified/deleteMany-rawdata.json
+rm $PYMONGO/test/crud/unified/deleteOne-rawdata.json
+rm $PYMONGO/test/crud/unified/distinct-rawdata.json
+rm $PYMONGO/test/crud/unified/estimatedDocumentCount-rawdata.json
+rm $PYMONGO/test/crud/unified/find-rawdata.json
+rm $PYMONGO/test/crud/unified/findOneAndDelete-rawdata.json
+rm $PYMONGO/test/crud/unified/findOneAndReplace-rawdata.json
+rm $PYMONGO/test/crud/unified/findOneAndUpdate-rawdata.json
+rm $PYMONGO/test/crud/unified/insertMany-rawdata.json
+rm $PYMONGO/test/crud/unified/insertOne-rawdata.json
+rm $PYMONGO/test/crud/unified/replaceOne-rawdata.json
+rm $PYMONGO/test/crud/unified/updateMany-rawdata.json
+rm $PYMONGO/test/crud/unified/updateOne-rawdata.json
+rm $PYMONGO/test/index_management/index-rawdata.json
+
+echo "done removing unimplemented tests"
diff --git a/.evergreen/resync-specs.sh b/.evergreen/resync-specs.sh
index d7dfafbba9..d567b380a6 100755
--- a/.evergreen/resync-specs.sh
+++ b/.evergreen/resync-specs.sh
@@ -45,9 +45,12 @@ then
 fi
 
 # Ensure the JSON files are up to date.
-cd $SPECS/source
-make
-cd -
+if ! [ -n "${CI:-}" ]
+then
+  cd $SPECS/source
+  make
+  cd -
+fi
 # cpjson unified-test-format/tests/invalid unified-test-format/invalid
 # * param1: Path to spec tests dir in specifications repo
 # * param2: Path to where the corresponding tests live in Python.
@@ -110,7 +113,6 @@ do
     cmap|CMAP|connection-monitoring-and-pooling)
       cpjson connection-monitoring-and-pooling/tests/logging connection_logging
       cpjson connection-monitoring-and-pooling/tests/cmap-format connection_monitoring
-      rm $PYMONGO/test/connection_monitoring/wait-queue-fairness.json  # PYTHON-1873
       ;;
     apm|APM|command-monitoring|command_monitoring)
       cpjson command-logging-and-monitoring/tests/monitoring command_monitoring
@@ -174,7 +176,6 @@ do
       ;;
     server-selection|server_selection)
       cpjson server-selection/tests/ server_selection
-      rm -rf $PYMONGO/test/server_selection/logging
       cpjson server-selection/tests/logging server_selection_logging
       ;;
     server-selection-logging|server_selection_logging)
@@ -186,7 +187,6 @@ do
     transactions|transactions-convenient-api)
       cpjson transactions/tests/ transactions
       cpjson transactions-convenient-api/tests/ transactions-convenient-api
-      rm $PYMONGO/test/transactions/legacy/errors-client.json  # PYTHON-1894
       ;;
     unified|unified-test-format)
       cpjson unified-test-format/tests/ unified-test-format/
diff --git a/.evergreen/scripts/create-pr.sh b/.evergreen/scripts/create-pr.sh
new file mode 100755
index 0000000000..a5e49bb211
--- /dev/null
+++ b/.evergreen/scripts/create-pr.sh
@@ -0,0 +1,50 @@
+#!/usr/bin/env bash
+
+tools="$(realpath -s "../drivers-tools")"
+pushd $tools/.evergreen/github_app || exit
+
+owner="mongodb"
+repo="mongo-python-driver"
+
+# Bootstrap the app.
+echo "bootstrapping"
+source utils.sh
+bootstrap drivers/comment-bot
+
+# Run the app.
+source ./secrets-export.sh
+
+# Get a github access token for the git checkout.
+echo "Getting github token..."
+
+token=$(bash ./get-access-token.sh $repo $owner)
+if [ -z "${token}" ]; then
+    echo "Failed to get github access token!"
+    popd || exit
+    exit 1
+fi
+echo "Getting github token... done."
+popd || exit
+
+# Make the git checkout and create a new branch.
+echo "Creating the git checkout..."
+branch="spec-resync-"$(date '+%m-%d-%Y')
+
+git remote set-url origin https://x-access-token:${token}@github.com/$owner/$repo.git
+git checkout -b $branch "origin/master"
+git add ./test
+git commit -am "resyncing specs $(date '+%m-%d-%Y')"
+echo "Creating the git checkout... done."
+
+git push origin $branch
+resp=$(curl -L \
+    -X POST \
+    -H "Accept: application/vnd.github+json" \
+    -H "Authorization: Bearer $token" \
+    -H "X-GitHub-Api-Version: 2022-11-28" \
+    -d "{\"title\":\"[Spec Resync] $(date '+%m-%d-%Y')\",\"body\":\"$(cat "$1")\",\"head\":\"${branch}\",\"base\":\"master\"}" \
+    --url https://api.github.com/repos/$owner/$repo/pulls)
+echo $resp | jq '.html_url'
+echo "Creating the PR... done."
+
+rm -rf $tools
diff --git a/.evergreen/scripts/resync-all-specs.py b/.evergreen/scripts/resync-all-specs.py
new file mode 100644
index 0000000000..347e51b310
--- /dev/null
+++ b/.evergreen/scripts/resync-all-specs.py
@@ -0,0 +1,109 @@
+from __future__ import annotations
+
+import argparse
+import os
+import pathlib
+import subprocess
+from subprocess import CalledProcessError
+
+
+def resync_specs(directory: pathlib.Path, errored: dict[str, str]) -> None:
+    """Actually sync the specs"""
+    for spec in os.scandir(directory):
+        if not spec.is_dir():
+            continue
+
+        if spec.name in ["asynchronous"]:
+            continue
+        try:
+            subprocess.run(
+                ["bash", "./.evergreen/resync-specs.sh", spec.name],  # noqa: S603, S607
+                capture_output=True,
+                text=True,
+                check=True,
+            )
+        except CalledProcessError as exc:
+            errored[spec.name] = exc.stderr
+
+
+def apply_patches():
+    subprocess.run(["bash", "./.evergreen/remove-unimplemented-tests.sh"], check=True)  # noqa: S603, S607
+    subprocess.run(["git apply -R --allow-empty ./.evergreen/patch/*"], shell=True, check=True)  # noqa: S602, S607
+
+
+def check_new_spec_directories(directory: pathlib.Path) -> list[str]:
+    """Check to see if there are any directories in the spec repo that don't exist in pymongo/test"""
+    spec_dir = pathlib.Path(os.environ["MDB_SPECS"]) / "source"
+    spec_set = {
+        entry.name.replace("-", "_")
+        for entry in os.scandir(spec_dir)
+        if entry.is_dir()
+        and (pathlib.Path(entry.path) / "tests").is_dir()
+        and len(list(os.scandir(pathlib.Path(entry.path) / "tests"))) > 1
+    }
+    test_set = {entry.name.replace("-", "_") for entry in os.scandir(directory) if entry.is_dir()}
+    known_mappings = {
+        "ocsp_support": "ocsp",
+        "client_side_operations_timeout": "csot",
+        "mongodb_handshake": "handshake",
+        "load_balancers": "load_balancer",
+        "atlas_data_lake_testing": "atlas",
+        "connection_monitoring_and_pooling": "connection_monitoring",
+        "command_logging_and_monitoring": "command_logging",
+        "initial_dns_seedlist_discovery": "srv_seedlist",
+        "server_discovery_and_monitoring": "sdam_monitoring",
+    }
+
+    for k, v in known_mappings.items():
+        if k in spec_set:
+            spec_set.remove(k)
+            spec_set.add(v)
+    return list(spec_set - test_set)
+
+
+def write_summary(errored: dict[str, str], new: list[str]) -> None:
+    """Generate the PR description"""
+    pr_body = ""
+    process = subprocess.run(
+        ["git diff --name-only | awk -F'/' '{print $2}' | sort | uniq"],  # noqa: S607
+        shell=True,  # noqa: S602
+        capture_output=True,
+        text=True,
+        check=True,
+    )
+    succeeded = [i for i in process.stdout.strip().split() if "data/mci/" not in i]
+    if len(succeeded) > 0:
+        pr_body += "The following specs were changed:\n -"
+        pr_body += "\n -".join(succeeded)
+        pr_body += "\n"
+    if len(errored) > 0:
+        pr_body += "\n\nThe following spec syncs encountered errors:\n -"
+        for k, v in errored.items():
+            pr_body += f"\n -{k}\n```{v}\n```"
+        pr_body += "\n"
+    if len(new) > 0:
+        pr_body += "\n\nThe following directories are in the specification repository and not in our test directory:\n -"
+        pr_body += "\n -".join(new)
+        pr_body += "\n"
+    if pr_body != "":
+        with open("spec_sync.txt", "w") as f:
+            # replacements made for proper json
+            f.write(pr_body.replace("\n", "\\n").replace("\t", "\\t"))
+
+
+def main():
+    directory = pathlib.Path("./test")
+    errored: dict[str, str] = {}
+    resync_specs(directory, errored)
+    apply_patches()
+    new = check_new_spec_directories(directory)
+    write_summary(errored, new)
+
+
+if __name__ == "__main__":
+    parser = argparse.ArgumentParser(
+        description="Python Script to resync all specs and generate summary for PR."
+    )
+    parser.add_argument("filename", help="Name of file for the summary to be written into.")
+    args = parser.parse_args()
+    main()
diff --git a/.evergreen/scripts/resync-all-specs.sh b/.evergreen/scripts/resync-all-specs.sh
new file mode 100755
index 0000000000..f0464ae6f2
--- /dev/null
+++ b/.evergreen/scripts/resync-all-specs.sh
@@ -0,0 +1,38 @@
+#!/usr/bin/env bash
+# Run spec syncing script and create PR
+
+# SETUP
+SRC_URL="https://github.com/mongodb/specifications.git"
+# needs to be set for resunc-specs.sh
+SPEC_SRC="$(realpath -s "../specifications")"
+SCRIPT="$(realpath -s "./.evergreen/resync-specs.sh")"
+
+# Clone the spec repo if the directory does not exist
+if [[ ! -d $SPEC_SRC ]]; then
+  git clone $SRC_URL $SPEC_SRC
+  if [[ $? -ne 0 ]]; then
+    echo "Error: Failed to clone repository."
+    exit 1
+  fi
+fi
+
+# Set environment variable to the cloned spec repo for resync-specs.sh
+export MDB_SPECS="$SPEC_SRC"
+
+# Check that resync-specs.sh exists and is executable
+if [[ ! -x $SCRIPT ]]; then
+  echo "Error: $SCRIPT not found or is not executable."
+  exit 1
+fi
+
+PR_DESC="spec_sync.txt"
+
+# run python script that actually does all the resyncing
+/opt/devtools/bin/python3.11 ./.evergreen/scripts/resync-all-specs.py "$PR_DESC"
+
+
+if [[ -f $PR_DESC ]]; then
+  # changes were made -> call scrypt to create PR for us
+  .evergreen/scripts/create-pr.sh "$PR_DESC"
+  rm "$PR_DESC"
+fi
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index ca98584602..994815b9cb 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -432,6 +432,40 @@ update in PyMongo. This is primarily helpful if you are implementing a
 new feature in PyMongo that has spec tests already implemented, or if
 you are attempting to validate new spec tests in PyMongo.
 
+### Automated Specification Test Resyncing
+There is a script (`/.evergreen/scripts/resync-all-specs.sh`) that will
+automatically run once a week to resync all the specs with the [specifications
+repo](https://github.com/mongodb/specifications).
+If there are changes, a PR will be generated by mongodb-drivers-pr-bot.
+If any errors occurred, the PR description will display the name of the spec along
+with stderr from the `bash resync-spec.sh <spec>` command.
+
+Naturally, there will be spec tests that will fail if merged since the associated fix
+or behavioral change has not been implemented yet. For existing tests that have been
+modified, we will add these changes to a patch file (in `/.evergreen/patch`). Each patch
+file will be named after a PYTHON ticket and the contents of the file will be the associated
+test differences between PyMongo's tests and the specification.
+To be clear, changes listed in these patch files will be *undone* by the script, and thus won't
+be added to pymongo.
+
+In the case that a new test is added to the spec repo (i.e., a whole new file or folder in the spec repo),
+and the associated work isn't implemented yet, we will add the test's path to
+`.evergreen/remove-unimplemented-tests.sh` along with a comment indicating the associated PYTHON ticket.
+
+These patch files and/or unimplemented paths must be removed as part of the PR that implements
+the fix or behavioral change.
+
+#### Adding to a patch file
+Assuming the changes are committed somewhere, to add to any of the
+patch files, run `git diff` to show the desired changes and paste the
+results into the patch file.
+
+For example, there are new test files on the most recent commit of the current branch that are failing.
+To add those changes to `new.patch`, I would do the following:
+```bash
+git diff HEAD~1 path/to/new/file >> .evergreen/patch/new.patch
+```
+
 ## Making a Release
 
 Follow the [Python Driver Release Process Wiki](https://wiki.corp.mongodb.com/display/DRIVERS/Python+Driver+Release+Process).