diff --git a/CHANGELOG.md b/CHANGELOG.md
index add505801..954deda3f 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@
 Unlock powerful malware analysis with capa's new [VMRay sandbox](https://www.vmray.com/) integration! Simply provide a VMRay analysis archive, and capa will automatically extract and match capabilties, streamlining your workflow.
 
 ### New Features
+- regenerate ruleset cache automatically on source change (only in dev mode) #2133 @s-ff
 
 - add landing page https://mandiant.github.io/capa/ @williballenthin #2310
 - add rules website https://mandiant.github.io/capa/rules @DeeyaSingh #2310
diff --git a/capa/helpers.py b/capa/helpers.py
index c0e5c5dcf..86f4db694 100644
--- a/capa/helpers.py
+++ b/capa/helpers.py
@@ -5,6 +5,7 @@
 # Unless required by applicable law or agreed to in writing, software distributed under the License
 #  is distributed on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and limitations under the License.
+import os
 import sys
 import gzip
 import inspect
@@ -14,6 +15,7 @@
 from typing import Dict, List, Union, BinaryIO, Iterator, NoReturn
 from pathlib import Path
 from zipfile import ZipFile
+from datetime import datetime
 
 import tqdm
 import msgspec.json
@@ -309,3 +311,62 @@ def is_running_standalone() -> bool:
     # so we keep this in a common area.
     # generally, other library code should not use this function.
     return hasattr(sys, "frozen") and hasattr(sys, "_MEIPASS")
+
+
+def is_dev_environment() -> bool:
+    if is_running_standalone():
+        return False
+
+    if "site-packages" in __file__:
+        # running from a site-packages installation
+        return False
+
+    capa_root = Path(__file__).resolve().parent.parent
+    git_dir = capa_root / ".git"
+
+    if not git_dir.is_dir():
+        # .git directory doesn't exist
+        return False
+
+    return True
+
+
+def is_cache_newer_than_rule_code(cache_dir: Path) -> bool:
+    """
+    basic check to prevent issues if the rules cache is older than relevant rules code
+
+    args:
+      cache_dir: the cache directory containing cache files
+
+    returns:
+      True if latest cache file is newer than relevant rule cache code
+    """
+
+    # retrieve the latest modified cache file
+    cache_files = list(cache_dir.glob("*.cache"))
+    if not cache_files:
+        logger.debug("no rule cache files found")
+        return False
+
+    latest_cache_file = max(cache_files, key=os.path.getmtime)
+    cache_timestamp = os.path.getmtime(latest_cache_file)
+
+    # these are the relevant rules code files that could conflict with using an outdated cache
+    latest_rule_code_file = max([Path("capa/rules/__init__.py"), Path("capa/rules/cache.py")], key=os.path.getmtime)
+    rule_code_timestamp = os.path.getmtime(latest_rule_code_file)
+
+    if rule_code_timestamp > cache_timestamp:
+
+        def ts_to_str(ts):
+            return datetime.fromtimestamp(ts).strftime("%Y-%m-%d %H:%M:%S")
+
+        logger.warning(
+            "latest rule code file %s (%s) is newer than the latest rule cache file %s (%s)",
+            latest_rule_code_file,
+            ts_to_str(rule_code_timestamp),
+            latest_cache_file,
+            ts_to_str(cache_timestamp),
+        )
+        return False
+
+    return True
diff --git a/capa/main.py b/capa/main.py
index 50afbb6c8..f6dc0f522 100644
--- a/capa/main.py
+++ b/capa/main.py
@@ -620,13 +620,22 @@ def get_rules_from_cli(args) -> RuleSet:
     raises:
       ShouldExitError: if the program is invoked incorrectly and should exit.
     """
+    enable_cache: bool = True
     try:
         if capa.helpers.is_running_standalone() and args.is_default_rules:
             cache_dir = get_default_root() / "cache"
         else:
             cache_dir = capa.rules.cache.get_default_cache_directory()
 
-        rules = capa.rules.get_rules(args.rules, cache_dir=cache_dir)
+        if capa.helpers.is_dev_environment():
+            # using the rules cache during development may result in unexpected errors, see #1898
+            enable_cache = capa.helpers.is_cache_newer_than_rule_code(cache_dir)
+            if not enable_cache:
+                logger.debug("not using cache. delete the cache file manually to use rule caching again")
+            else:
+                logger.debug("cache can be used, no potentially outdated cache files found")
+
+        rules = capa.rules.get_rules(args.rules, cache_dir=cache_dir, enable_cache=enable_cache)
     except (IOError, capa.rules.InvalidRule, capa.rules.InvalidRuleSet) as e:
         logger.error("%s", str(e))
         logger.error(
diff --git a/capa/rules/__init__.py b/capa/rules/__init__.py
index 5ecad5cce..1d7f13ed1 100644
--- a/capa/rules/__init__.py
+++ b/capa/rules/__init__.py
@@ -2130,12 +2130,14 @@ def get_rules(
     rule_paths: List[RulePath],
     cache_dir=None,
     on_load_rule: Callable[[RulePath, int, int], None] = on_load_rule_default,
+    enable_cache: bool = True,
 ) -> RuleSet:
     """
     args:
       rule_paths: list of paths to rules files or directories containing rules files
       cache_dir: directory to use for caching rules, or will use the default detected cache directory if None
       on_load_rule: callback to invoke before a rule is loaded, use for progress or cancellation
+      enable_cache: enable loading of a cached ruleset (default: True)
     """
     if cache_dir is None:
         cache_dir = capa.rules.cache.get_default_cache_directory()
@@ -2147,9 +2149,10 @@ def get_rules(
     # rule_file_paths[i] corresponds to rule_contents[i].
     rule_contents = [file_path.read_bytes() for file_path in rule_file_paths]
 
-    ruleset = capa.rules.cache.load_cached_ruleset(cache_dir, rule_contents)
-    if ruleset is not None:
-        return ruleset
+    if enable_cache:
+        ruleset = capa.rules.cache.load_cached_ruleset(cache_dir, rule_contents)
+        if ruleset is not None:
+            return ruleset
 
     rules: List[Rule] = []
 
diff --git a/tests/test_helpers.py b/tests/test_helpers.py
index 3f3fc9325..1f291f7ee 100644
--- a/tests/test_helpers.py
+++ b/tests/test_helpers.py
@@ -8,6 +8,7 @@
 
 import codecs
 
+import capa.helpers
 from capa.features.extractors import helpers
 
 
@@ -64,3 +65,8 @@ def test_generate_symbols():
     symbols = list(helpers.generate_symbols("ws2_32", "#1", include_dll=False))
     assert len(symbols) == 1
     assert "ws2_32.#1" in symbols
+
+
+def test_is_dev_environment():
+    # testing environment should be a dev environment
+    assert capa.helpers.is_dev_environment() is True
diff --git a/tests/test_rule_cache.py b/tests/test_rule_cache.py
index 0206e936d..b694b98c4 100644
--- a/tests/test_rule_cache.py
+++ b/tests/test_rule_cache.py
@@ -6,10 +6,13 @@
 #  is distributed on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and limitations under the License.
 
+import os
 import textwrap
 import contextlib
+from pathlib import Path
 
 import capa.rules
+import capa.helpers
 import capa.rules.cache
 
 R1 = capa.rules.Rule.from_yaml(
@@ -113,3 +116,40 @@ def test_ruleset_cache_invalid():
     assert capa.rules.cache.load_cached_ruleset(cache_dir, content) is None
     # the invalid cache should be deleted
     assert not path.exists()
+
+
+def test_rule_cache_dev_environment():
+    # generate rules cache
+    rs = capa.rules.RuleSet([R2])
+    content = capa.rules.cache.get_ruleset_content(rs)
+    id = capa.rules.cache.compute_cache_identifier(content)
+    cache_dir = capa.rules.cache.get_default_cache_directory()
+    cache_path = capa.rules.cache.get_cache_path(cache_dir, id)
+
+    # clear existing cache files
+    for f in cache_dir.glob("*.cache"):
+        f.unlink()
+
+    capa.rules.cache.cache_ruleset(cache_dir, rs)
+    assert cache_path.exists()
+
+    assert capa.helpers.is_cache_newer_than_rule_code(cache_dir) is True
+
+    capa_root = Path(__file__).resolve().parent.parent
+    cachepy = capa_root / "capa" / "rules" / "cache.py"  # alternative: capa_root / "capa" / "rules" / "__init__.py"
+
+    # set cache's last modified time prior to code file's modified time
+    os.utime(cache_path, (cache_path.stat().st_atime, cachepy.stat().st_mtime - 600000))
+
+    # debug
+    def ts_to_str(ts):
+        from datetime import datetime
+
+        return datetime.fromtimestamp(ts).strftime("%Y-%m-%d %H:%M:%S")
+
+    for g in ((capa_root / "capa" / "rules").glob("*.py"), cache_dir.glob("*.cache")):
+        for p in g:
+            print(p, "\t", ts_to_str(p.stat().st_mtime))  # noqa: T201
+
+    assert capa.helpers.is_dev_environment() is True
+    assert capa.helpers.is_cache_newer_than_rule_code(cache_dir) is False
diff --git a/web/explorer/src/utils/rdocParser.js b/web/explorer/src/utils/rdocParser.js
index 61885308f..d5ca6dfdb 100644
--- a/web/explorer/src/utils/rdocParser.js
+++ b/web/explorer/src/utils/rdocParser.js
@@ -490,6 +490,8 @@ function getFeatureName(feature) {
             return formatBytes(feature.bytes);
         case "operand offset":
             return `operand[${feature.index}].offset: 0x${feature.operand_offset.toString(16).toUpperCase()}`;
+        case "class":
+            return `${feature.class_}`;
         default:
             return `${feature[feature.type]}`;
     }