diff --git a/.github/workflows/ci_pipeline.yml b/.github/workflows/ci_pipeline.yml
index d7ed929..8370a7d 100644
--- a/.github/workflows/ci_pipeline.yml
+++ b/.github/workflows/ci_pipeline.yml
@@ -23,7 +23,7 @@ jobs:
     strategy:
       matrix:
         os: [ubuntu-latest]
-        python-version: ["3.9"]
+        python-version: ["3.10"]
     steps:
       - uses: actions/checkout@v4
       - uses: ./.github/actions/setup
@@ -39,7 +39,7 @@ jobs:
     strategy:
       matrix:
         os: [macos-latest, windows-latest]
-        python-version: ["3.9"]
+        python-version: ["3.10"]
     steps:
       - uses: actions/checkout@v4
       - uses: ./.github/actions/setup
@@ -55,7 +55,7 @@ jobs:
     strategy:
       matrix:
         os: [ubuntu-latest]
-        python-version: ["3.9"]
+        python-version: ["3.10"]
     steps:
       - uses: actions/checkout@v4
       - uses: ./.github/actions/setup
diff --git a/docs/docs/CHANGELOG.md b/docs/docs/CHANGELOG.md
index 64e2279..5f99193 100644
--- a/docs/docs/CHANGELOG.md
+++ b/docs/docs/CHANGELOG.md
@@ -1,3 +1,9 @@
+## Unreleased
+
+### Feat
+
+- implement --debug flag for troubleshooting
+
 ## 1.4.2 (2025-09-10)
 
 ### Fix
diff --git a/docs/docs/CODE_TAG_SUMMARY.md b/docs/docs/CODE_TAG_SUMMARY.md
index 44642d3..814a4d7 100644
--- a/docs/docs/CODE_TAG_SUMMARY.md
+++ b/docs/docs/CODE_TAG_SUMMARY.md
@@ -1,12 +1,11 @@
 # Collected Code Tags
 
-| Type    | Comment                                                          | Last Edit  | Source File                                                                                                                                             |
-|---------|------------------------------------------------------------------|------------|---------------------------------------------------------------------------------------------------------------------------------------------------------|
-| PLANNED | Consider moving to Corallium                                     | 2025-09-11 | [tail_jsonl/_private/core.py:75](https://github.com/KyleKing/tail-jsonl/blame/b8b654530a8750cb53a399e368689168e3cc2123/tail_jsonl/_private/core.py#L75) |
-| PLANNED | temporary backward compatibility until part of Corallium         | 2024-10-05 | [tail_jsonl/config.py:10](https://github.com/KyleKing/tail-jsonl/blame/bd32054c9276da9dba500cb7c1289061f4e0ada1/tail_jsonl/config.py#L10)               |
-| TODO    | Are these dotted keys properly parsed?                           | 2025-09-11 | [tail_jsonl/config.py:22](https://github.com/KyleKing/tail-jsonl/blame/57ebf0b3404ebd5daf4f45933267f38b40ae3738/tail_jsonl/config.py#L22)               |
-| PLANNED | Add a flag (--debug & store_true) to print debugging information | 2023-02-02 | [tail_jsonl/scripts.py:29](https://github.com/KyleKing/tail-jsonl/blame/fd15e5907afae783ba21bb0f9d310cc6b08008c4/tail_jsonl/main.py#L34)                |
+| Type    | Comment                                                  | Last Edit  | Source File                                                                                                                                             |
+|---------|----------------------------------------------------------|------------|---------------------------------------------------------------------------------------------------------------------------------------------------------|
+| PLANNED | Consider moving to Corallium                             | 2025-09-11 | [tail_jsonl/_private/core.py:89](https://github.com/KyleKing/tail-jsonl/blame/b8b654530a8750cb53a399e368689168e3cc2123/tail_jsonl/_private/core.py#L75) |
+| PLANNED | temporary backward compatibility until part of Corallium | 2024-10-05 | [tail_jsonl/config.py:10](https://github.com/KyleKing/tail-jsonl/blame/bd32054c9276da9dba500cb7c1289061f4e0ada1/tail_jsonl/config.py#L10)               |
+| TODO    | Are these dotted keys properly parsed?                   | 2025-09-11 | [tail_jsonl/config.py:22](https://github.com/KyleKing/tail-jsonl/blame/57ebf0b3404ebd5daf4f45933267f38b40ae3738/tail_jsonl/config.py#L22)               |
 
-Found code tags for TODO (1), PLANNED (3)
+Found code tags for TODO (1), PLANNED (2)
 
 <!-- calcipy_skip_tags -->
diff --git a/docs/docs/DEVELOPER_GUIDE.md b/docs/docs/DEVELOPER_GUIDE.md
index d66c7c2..11dd13d 100644
--- a/docs/docs/DEVELOPER_GUIDE.md
+++ b/docs/docs/DEVELOPER_GUIDE.md
@@ -49,11 +49,11 @@ poetry config pypi-token.pypi ...
 |-------------------------------------------|-----------:|--------:|---------:|---------:|
 | `tail_jsonl/__init__.py`                  | 4          | 0       | 0        | 100.0%   |
 | `tail_jsonl/_private/__init__.py`         | 0          | 0       | 0        | 100.0%   |
-| `tail_jsonl/_private/core.py`             | 54         | 1       | 0        | 97.0%    |
+| `tail_jsonl/_private/core.py`             | 59         | 4       | 0        | 89.9%    |
 | `tail_jsonl/_runtime_type_check_setup.py` | 13         | 0       | 37       | 100.0%   |
-| `tail_jsonl/config.py`                    | 23         | 0       | 0        | 100.0%   |
-| `tail_jsonl/scripts.py`                   | 16         | 0       | 18       | 94.4%    |
-| **Totals**                                | 110        | 1       | 55       | 97.6%    |
+| `tail_jsonl/config.py`                    | 24         | 0       | 0        | 100.0%   |
+| `tail_jsonl/scripts.py`                   | 19         | 1       | 20       | 87.0%    |
+| **Totals**                                | 119        | 5       | 57       | 92.4%    |
 
-Generated on: 2025-09-10
+Generated on: 2025-11-21
 <!-- {cte} -->
diff --git a/poetry.lock b/poetry.lock
index e767a80..58e48a1 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -373,7 +373,6 @@ charset-normalizer = ">=2.1.0,<4"
 colorama = ">=0.4.1,<1.0"
 decli = ">=0.6.0,<1.0"
 deprecated = ">=1.2.13,<2"
-importlib-metadata = {version = ">=8.0.0,<8.7.0", markers = "python_version < \"3.10\""}
 jinja2 = ">=2.10.3"
 packaging = ">=19"
 prompt_toolkit = "!=3.0.52"
@@ -401,127 +400,6 @@ rich = ">=13.9.2"
 tomli = {version = ">=2.0.2", markers = "python_version < \"3.11\""}
 typing-extensions = ">=4.12.2"
 
-[[package]]
-name = "coverage"
-version = "7.10.7"
-description = "Code coverage measurement for Python"
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
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-]
-
-[package.dependencies]
-tomli = {version = "*", optional = true, markers = "python_full_version <= \"3.11.0a6\" and extra == \"toml\""}
-
-[package.extras]
-toml = ["tomli ; python_full_version <= \"3.11.0a6\""]
-
 [[package]]
 name = "coverage"
 version = "7.12.0"
@@ -529,7 +407,6 @@ description = "Code coverage measurement for Python"
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "coverage-7.12.0-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:32b75c2ba3f324ee37af3ccee5b30458038c50b349ad9b88cee85096132a575b"},
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@@ -725,19 +602,6 @@ typing-extensions = {version = ">=4.6.0", markers = "python_version < \"3.13\""}
 [package.extras]
 test = ["pytest (>=6)"]
 
-[[package]]
-name = "filelock"
-version = "3.19.1"
-description = "A platform independent file lock."
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "filelock-3.19.1-py3-none-any.whl", hash = "sha256:d38e30481def20772f5baf097c122c3babc4fcdb7e14e57049eb9d88c6dc017d"},
-    {file = "filelock-3.19.1.tar.gz", hash = "sha256:66eda1888b0171c998b35be2bcc0f6d75c388a7ce20c3f3f37aa8e96c2dddf58"},
-]
-
 [[package]]
 name = "filelock"
 version = "3.20.0"
@@ -745,7 +609,6 @@ description = "A platform independent file lock."
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "filelock-3.20.0-py3-none-any.whl", hash = "sha256:339b4732ffda5cd79b13f4e2711a31b0365ce445d95d243bb996273d072546a2"},
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@@ -769,22 +632,6 @@ python-dateutil = ">=2.8.1"
 [package.extras]
 dev = ["flake8", "markdown", "twine", "wheel"]
 
-[[package]]
-name = "griffe"
-version = "1.14.0"
-description = "Signatures for entire Python programs. Extract the structure, the frame, the skeleton of your project, to generate API documentation or find breaking changes in your API."
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "griffe-1.14.0-py3-none-any.whl", hash = "sha256:0e9d52832cccf0f7188cfe585ba962d2674b241c01916d780925df34873bceb0"},
-    {file = "griffe-1.14.0.tar.gz", hash = "sha256:9d2a15c1eca966d68e00517de5d69dd1bc5c9f2335ef6c1775362ba5b8651a13"},
-]
-
-[package.dependencies]
-colorama = ">=0.4"
-
 [[package]]
 name = "griffe"
 version = "1.15.0"
@@ -792,7 +639,6 @@ description = "Signatures for entire Python programs. Extract the structure, the
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "griffe-1.15.0-py3-none-any.whl", hash = "sha256:6f6762661949411031f5fcda9593f586e6ce8340f0ba88921a0f2ef7a81eb9a3"},
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@@ -804,22 +650,6 @@ colorama = ">=0.4"
 [package.extras]
 pypi = ["pip (>=24.0)", "platformdirs (>=4.2)", "wheel (>=0.42)"]
 
-[[package]]
-name = "humanize"
-version = "4.13.0"
-description = "Python humanize utilities"
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "humanize-4.13.0-py3-none-any.whl", hash = "sha256:b810820b31891813b1673e8fec7f1ed3312061eab2f26e3fa192c393d11ed25f"},
-    {file = "humanize-4.13.0.tar.gz", hash = "sha256:78f79e68f76f0b04d711c4e55d32bebef5be387148862cb1ef83d2b58e7935a0"},
-]
-
-[package.extras]
-tests = ["freezegun", "pytest", "pytest-cov"]
-
 [[package]]
 name = "humanize"
 version = "4.14.0"
@@ -827,7 +657,6 @@ description = "Python humanize utilities"
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "humanize-4.14.0-py3-none-any.whl", hash = "sha256:d57701248d040ad456092820e6fde56c930f17749956ac47f4f655c0c547bfff"},
     {file = "humanize-4.14.0.tar.gz", hash = "sha256:2fa092705ea640d605c435b1ca82b2866a1b601cdf96f076d70b79a855eba90d"},
@@ -851,31 +680,6 @@ files = [
 [package.extras]
 all = ["flake8 (>=7.1.1)", "mypy (>=1.11.2)", "pytest (>=8.3.2)", "ruff (>=0.6.2)"]
 
-[[package]]
-name = "importlib-metadata"
-version = "8.6.1"
-description = "Read metadata from Python packages"
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "importlib_metadata-8.6.1-py3-none-any.whl", hash = "sha256:02a89390c1e15fdfdc0d7c6b25cb3e62650d0494005c97d6f148bf5b9787525e"},
-    {file = "importlib_metadata-8.6.1.tar.gz", hash = "sha256:310b41d755445d74569f993ccfc22838295d9fe005425094fad953d7f15c8580"},
-]
-
-[package.dependencies]
-zipp = ">=3.20"
-
-[package.extras]
-check = ["pytest-checkdocs (>=2.4)", "pytest-ruff (>=0.2.1) ; sys_platform != \"cygwin\""]
-cover = ["pytest-cov"]
-doc = ["furo", "jaraco.packaging (>=9.3)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
-enabler = ["pytest-enabler (>=2.2)"]
-perf = ["ipython"]
-test = ["flufl.flake8", "importlib_resources (>=1.3) ; python_version < \"3.9\"", "jaraco.test (>=5.4)", "packaging", "pyfakefs", "pytest (>=6,!=8.1.*)", "pytest-perf (>=0.9.2)"]
-type = ["pytest-mypy"]
-
 [[package]]
 name = "importlib-metadata"
 version = "8.7.0"
@@ -883,7 +687,7 @@ description = "Read metadata from Python packages"
 optional = false
 python-versions = ">=3.9"
 groups = ["dev"]
-markers = "python_version >= \"3.10\" and python_full_version < \"3.10.2\""
+markers = "python_full_version < \"3.10.2\""
 files = [
     {file = "importlib_metadata-8.7.0-py3-none-any.whl", hash = "sha256:e5dd1551894c77868a30651cef00984d50e1002d06942a7101d34870c5f02afd"},
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@@ -901,19 +705,6 @@ perf = ["ipython"]
 test = ["flufl.flake8", "importlib_resources (>=1.3) ; python_version < \"3.9\"", "jaraco.test (>=5.4)", "packaging", "pyfakefs", "pytest (>=6,!=8.1.*)", "pytest-perf (>=0.9.2)"]
 type = ["pytest-mypy"]
 
-[[package]]
-name = "iniconfig"
-version = "2.1.0"
-description = "brain-dead simple config-ini parsing"
-optional = false
-python-versions = ">=3.8"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
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-    {file = "iniconfig-2.1.0.tar.gz", hash = "sha256:3abbd2e30b36733fee78f9c7f7308f2d0050e88f0087fd25c2645f63c773e1c7"},
-]
-
 [[package]]
 name = "iniconfig"
 version = "2.3.0"
@@ -921,7 +712,6 @@ description = "brain-dead simple config-ini parsing"
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "iniconfig-2.3.0-py3-none-any.whl", hash = "sha256:f631c04d2c48c52b84d0d0549c99ff3859c98df65b3101406327ecc7d53fbf12"},
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@@ -957,26 +747,6 @@ MarkupSafe = ">=2.0"
 [package.extras]
 i18n = ["Babel (>=2.7)"]
 
-[[package]]
-name = "markdown"
-version = "3.9"
-description = "Python implementation of John Gruber's Markdown."
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "markdown-3.9-py3-none-any.whl", hash = "sha256:9f4d91ed810864ea88a6f32c07ba8bee1346c0cc1f6b1f9f6c822f2a9667d280"},
-    {file = "markdown-3.9.tar.gz", hash = "sha256:d2900fe1782bd33bdbbd56859defef70c2e78fc46668f8eb9df3128138f2cb6a"},
-]
-
-[package.dependencies]
-importlib-metadata = {version = ">=4.4", markers = "python_version < \"3.10\""}
-
-[package.extras]
-docs = ["mdx_gh_links (>=0.2)", "mkdocs (>=1.6)", "mkdocs-gen-files", "mkdocs-literate-nav", "mkdocs-nature (>=0.6)", "mkdocs-section-index", "mkdocstrings[python]"]
-testing = ["coverage", "pyyaml"]
-
 [[package]]
 name = "markdown"
 version = "3.10"
@@ -984,7 +754,6 @@ description = "Python implementation of John Gruber's Markdown."
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "markdown-3.10-py3-none-any.whl", hash = "sha256:b5b99d6951e2e4948d939255596523444c0e677c669700b1d17aa4a8a464cb7c"},
     {file = "markdown-3.10.tar.gz", hash = "sha256:37062d4f2aa4b2b6b32aefb80faa300f82cc790cb949a35b8caede34f2b68c0e"},
@@ -1158,7 +927,6 @@ files = [
 click = ">=7.0"
 colorama = {version = ">=0.4", markers = "platform_system == \"Windows\""}
 ghp-import = ">=1.0"
-importlib-metadata = {version = ">=4.4", markers = "python_version < \"3.10\""}
 jinja2 = ">=2.11.1"
 markdown = ">=3.3.6"
 markupsafe = ">=2.0.1"
@@ -1219,7 +987,6 @@ files = [
 ]
 
 [package.dependencies]
-importlib-metadata = {version = ">=4.3", markers = "python_version < \"3.10\""}
 mergedeep = ">=1.3.4"
 platformdirs = ">=2.2.0"
 pyyaml = ">=5.1"
@@ -1279,7 +1046,6 @@ files = [
 ]
 
 [package.dependencies]
-importlib-metadata = {version = ">=4.6", markers = "python_version < \"3.10\""}
 Jinja2 = ">=2.11.1"
 Markdown = ">=3.6"
 MarkupSafe = ">=1.1"
@@ -1293,25 +1059,6 @@ crystal = ["mkdocstrings-crystal (>=0.3.4)"]
 python = ["mkdocstrings-python (>=1.16.2)"]
 python-legacy = ["mkdocstrings-python-legacy (>=0.2.1)"]
 
-[[package]]
-name = "mkdocstrings-python"
-version = "1.18.2"
-description = "A Python handler for mkdocstrings."
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "mkdocstrings_python-1.18.2-py3-none-any.whl", hash = "sha256:944fe6deb8f08f33fa936d538233c4036e9f53e840994f6146e8e94eb71b600d"},
-    {file = "mkdocstrings_python-1.18.2.tar.gz", hash = "sha256:4ad536920a07b6336f50d4c6d5603316fafb1172c5c882370cbbc954770ad323"},
-]
-
-[package.dependencies]
-griffe = ">=1.13"
-mkdocs-autorefs = ">=1.4"
-mkdocstrings = ">=0.30"
-typing-extensions = {version = ">=4.0", markers = "python_version < \"3.11\""}
-
 [[package]]
 name = "mkdocstrings-python"
 version = "1.19.0"
@@ -1319,7 +1066,6 @@ description = "A Python handler for mkdocstrings."
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "mkdocstrings_python-1.19.0-py3-none-any.whl", hash = "sha256:395c1032af8f005234170575cc0c5d4d20980846623b623b35594281be4a3059"},
     {file = "mkdocstrings_python-1.19.0.tar.gz", hash = "sha256:917aac66cf121243c11db5b89f66b0ded6c53ec0de5318ff5e22424eb2f2e57c"},
@@ -1422,15 +1168,9 @@ attrs = ">=24.1"
 colorlog = ">=2.6.1,<7"
 dependency-groups = ">=1.1"
 humanize = ">=4"
-packaging = [
-    {version = ">=20.9", markers = "python_version < \"3.10\""},
-    {version = ">=21", markers = "python_version >= \"3.10\""},
-]
+packaging = {version = ">=21", markers = "python_version >= \"3.10\""}
 tomli = {version = ">=1.1", markers = "python_version < \"3.11\""}
-virtualenv = [
-    {version = ">=20.14.1", markers = "python_version < \"3.10\""},
-    {version = ">=20.15", markers = "python_version >= \"3.10\""},
-]
+virtualenv = {version = ">=20.15", markers = "python_version >= \"3.10\""}
 
 [package.extras]
 pbs = ["pbs-installer[all] (>=2025.1.6)"]
@@ -1495,24 +1235,6 @@ files = [
     {file = "pathspec-0.12.1.tar.gz", hash = "sha256:a482d51503a1ab33b1c67a6c3813a26953dbdc71c31dacaef9a838c4e29f5712"},
 ]
 
-[[package]]
-name = "platformdirs"
-version = "4.4.0"
-description = "A small Python package for determining appropriate platform-specific dirs, e.g. a `user data dir`."
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "platformdirs-4.4.0-py3-none-any.whl", hash = "sha256:abd01743f24e5287cd7a5db3752faf1a2d65353f38ec26d98e25a6db65958c85"},
-    {file = "platformdirs-4.4.0.tar.gz", hash = "sha256:ca753cf4d81dc309bc67b0ea38fd15dc97bc30ce419a7f58d13eb3bf14c4febf"},
-]
-
-[package.extras]
-docs = ["furo (>=2024.8.6)", "proselint (>=0.14)", "sphinx (>=8.1.3)", "sphinx-autodoc-typehints (>=3)"]
-test = ["appdirs (==1.4.4)", "covdefaults (>=2.3)", "pytest (>=8.3.4)", "pytest-cov (>=6)", "pytest-mock (>=3.14)"]
-type = ["mypy (>=1.14.1)"]
-
 [[package]]
 name = "platformdirs"
 version = "4.5.0"
@@ -1520,7 +1242,6 @@ description = "A small Python package for determining appropriate platform-speci
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "platformdirs-4.5.0-py3-none-any.whl", hash = "sha256:e578a81bb873cbb89a41fcc904c7ef523cc18284b7e3b3ccf06aca1403b7ebd3"},
     {file = "platformdirs-4.5.0.tar.gz", hash = "sha256:70ddccdd7c99fc5942e9fc25636a8b34d04c24b335100223152c2803e4063312"},
@@ -1623,31 +1344,6 @@ files = [
     {file = "pyproject_hooks-1.2.0.tar.gz", hash = "sha256:1e859bd5c40fae9448642dd871adf459e5e2084186e8d2c2a79a824c970da1f8"},
 ]
 
-[[package]]
-name = "pytest"
-version = "8.4.2"
-description = "pytest: simple powerful testing with Python"
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "pytest-8.4.2-py3-none-any.whl", hash = "sha256:872f880de3fc3a5bdc88a11b39c9710c3497a547cfa9320bc3c5e62fbf272e79"},
-    {file = "pytest-8.4.2.tar.gz", hash = "sha256:86c0d0b93306b961d58d62a4db4879f27fe25513d4b969df351abdddb3c30e01"},
-]
-
-[package.dependencies]
-colorama = {version = ">=0.4", markers = "sys_platform == \"win32\""}
-exceptiongroup = {version = ">=1", markers = "python_version < \"3.11\""}
-iniconfig = ">=1"
-packaging = ">=20"
-pluggy = ">=1.5,<2"
-pygments = ">=2.7.2"
-tomli = {version = ">=1", markers = "python_version < \"3.11\""}
-
-[package.extras]
-dev = ["argcomplete", "attrs (>=19.2)", "hypothesis (>=3.56)", "mock", "requests", "setuptools", "xmlschema"]
-
 [[package]]
 name = "pytest"
 version = "9.0.1"
@@ -1655,7 +1351,6 @@ description = "pytest: simple powerful testing with Python"
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "pytest-9.0.1-py3-none-any.whl", hash = "sha256:67be0030d194df2dfa7b556f2e56fb3c3315bd5c8822c6951162b92b32ce7dad"},
     {file = "pytest-9.0.1.tar.gz", hash = "sha256:3e9c069ea73583e255c3b21cf46b8d3c56f6e3a1a8f6da94ccb0fcf57b9d73c8"},
@@ -1706,7 +1401,6 @@ files = [
 ]
 
 [package.dependencies]
-importlib-metadata = {version = ">=3.6", markers = "python_version < \"3.10\""}
 pytest = "*"
 
 [[package]]
@@ -1935,22 +1629,6 @@ files = [
     {file = "six-1.17.0.tar.gz", hash = "sha256:ff70335d468e7eb6ec65b95b99d3a2836546063f63acc5171de367e834932a81"},
 ]
 
-[[package]]
-name = "syrupy"
-version = "4.9.1"
-description = "Pytest Snapshot Test Utility"
-optional = false
-python-versions = ">=3.8.1"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "syrupy-4.9.1-py3-none-any.whl", hash = "sha256:b94cc12ed0e5e75b448255430af642516842a2374a46936dd2650cfb6dd20eda"},
-    {file = "syrupy-4.9.1.tar.gz", hash = "sha256:b7d0fcadad80a7d2f6c4c71917918e8ebe2483e8c703dfc8d49cdbb01081f9a4"},
-]
-
-[package.dependencies]
-pytest = ">=7.0.0,<9.0.0"
-
 [[package]]
 name = "syrupy"
 version = "5.0.0"
@@ -1958,7 +1636,6 @@ description = "Pytest Snapshot Test Utility"
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "syrupy-5.0.0-py3-none-any.whl", hash = "sha256:c848e1a980ca52a28715cd2d2b4d434db424699c05653bd1158fb31cf56e9546"},
     {file = "syrupy-5.0.0.tar.gz", hash = "sha256:3282fe963fa5d4d3e47231b16d1d4d0f4523705e8199eeb99a22a1bc9f5942f2"},
@@ -1967,22 +1644,6 @@ files = [
 [package.dependencies]
 pytest = ">=8.0.0"
 
-[[package]]
-name = "termcolor"
-version = "3.1.0"
-description = "ANSI color formatting for output in terminal"
-optional = false
-python-versions = ">=3.9"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
-    {file = "termcolor-3.1.0-py3-none-any.whl", hash = "sha256:591dd26b5c2ce03b9e43f391264626557873ce1d379019786f99b0c2bee140aa"},
-    {file = "termcolor-3.1.0.tar.gz", hash = "sha256:6a6dd7fbee581909eeec6a756cff1d7f7c376063b14e4a298dc4980309e55970"},
-]
-
-[package.extras]
-tests = ["pytest", "pytest-cov"]
-
 [[package]]
 name = "termcolor"
 version = "3.2.0"
@@ -1990,7 +1651,6 @@ description = "ANSI color formatting for output in terminal"
 optional = false
 python-versions = ">=3.10"
 groups = ["dev"]
-markers = "python_version >= \"3.10\""
 files = [
     {file = "termcolor-3.2.0-py3-none-any.whl", hash = "sha256:a10343879eba4da819353c55cb8049b0933890c2ebf9ad5d3ecd2bb32ea96ea6"},
     {file = "termcolor-3.2.0.tar.gz", hash = "sha256:610e6456feec42c4bcd28934a8c87a06c3fa28b01561d46aa09a9881b8622c58"},
@@ -2328,5 +1988,5 @@ type = ["pytest-mypy"]
 
 [metadata]
 lock-version = "2.1"
-python-versions = "^3.9.13"
-content-hash = "84d0eb93bf07b60587de06f3a041b619db2e7ad54413aed34ceea6ac576f7a39"
+python-versions = "^3.10.0"
+content-hash = "156defd316aab1f111f7e8438520c23d50992332ad9d8023dd59c9662db878af"
diff --git a/pyproject.toml b/pyproject.toml
index 70a9e7b..c90afd4 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -15,7 +15,7 @@ files = ["tail_jsonl", "tests"]
 no_implicit_reexport = true
 plugins = [
 ]
-python_version = "3.9"
+python_version = "3.10"
 show_column_numbers = true
 show_error_codes = true
 strict_equality = true
@@ -34,7 +34,6 @@ classifiers = [
   "Programming Language :: Python :: 3.10",
   "Programming Language :: Python :: 3.11",
   "Programming Language :: Python :: 3.12",
-  "Programming Language :: Python :: 3.9",
 ] # https://pypi.org/classifiers/
 description = "Pretty Print Tailed JSONL Logs"
 documentation = "https://tail-jsonl.kyleking.me"
@@ -47,7 +46,7 @@ repository = "https://github.com/kyleking/tail-jsonl"
 version = "1.4.2"
 
 [tool.poetry.dependencies]
-python = "^3.9.13"
+python = "^3.10.0"
 corallium = ">=2.1.1"
 dotted-notation = ">=0.11.0"
 
@@ -65,13 +64,13 @@ tail-jsonl = "tail_jsonl.scripts:start"
 
 [tool.pyright]
 include = ["tail_jsonl", "tests"]
-pythonVersion = "3.9"
+pythonVersion = "3.10"
 
 [tool.ruff]
 # Docs: https://github.com/charliermarsh/ruff
 # Tip: poetry run python -m ruff rule RUF100
 line-length = 120
-target-version = 'py39'
+target-version = 'py310'
 
 [tool.ruff.lint]
 ignore = [
diff --git a/tail_jsonl/_private/core.py b/tail_jsonl/_private/core.py
index 7c23cef..0b5e0e2 100644
--- a/tail_jsonl/_private/core.py
+++ b/tail_jsonl/_private/core.py
@@ -62,9 +62,24 @@ def from_line(cls, data: dict, config: Config) -> Record:  # type: ignore[type-a
 def print_record(line: str, console: Console, config: Config) -> None:
     """Format and print the record."""
     try:
-        record = Record.from_line(json.loads(line), config=config)
-    except (json.JSONDecodeError, ValueError, KeyError, TypeError, AttributeError):
-        # Handle JSON parsing errors, missing keys, type errors, and attribute access issues
+        data = json.loads(line)
+        record = Record.from_line(data, config=config)
+        if config.debug:
+            console.print(
+                (
+                    f'[dim]DEBUG: Parsed keys - timestamp={record.timestamp!r},'
+                    f' level={record.level!r}, message={record.message!r}[/dim]'
+                ),
+                markup=True,
+                highlight=False,
+            )
+    except (json.JSONDecodeError, ValueError, KeyError, TypeError, AttributeError) as exc:
+        if config.debug:
+            console.print(
+                f'[dim red]DEBUG: Failed to parse line as JSON: {exc.__class__.__name__}: {exc}[/dim red]',
+                markup=True,
+                highlight=False,
+            )
         console.print(line.rstrip(), markup=False, highlight=False)  # Print the unmodified line
         return
 
@@ -76,6 +91,12 @@ def print_record(line: str, console: Console, config: Config) -> None:
         if '.' not in dotted_key:
             continue
         if value := dotted.get(record.data, dotted_key):
+            if config.debug:
+                console.print(
+                    f'[dim]DEBUG: Promoting dotted key {dotted_key!r} to own line[/dim]',
+                    markup=True,
+                    highlight=False,
+                )
             record.data[dotted_key] = value if isinstance(value, str) else str(value)
             dotted.remove(record.data, dotted_key)
 
diff --git a/tail_jsonl/config.py b/tail_jsonl/config.py
index 0bb8994..79e6b48 100644
--- a/tail_jsonl/config.py
+++ b/tail_jsonl/config.py
@@ -38,6 +38,7 @@ class Config:
 
     styles: Styles = field(default_factory=Styles)
     keys: Keys = field(default_factory=Keys)
+    debug: bool = False
 
     @classmethod
     def from_dict(cls, data: dict) -> Config:  # type: ignore[type-arg]
@@ -45,4 +46,5 @@ def from_dict(cls, data: dict) -> Config:  # type: ignore[type-arg]
         return cls(
             styles=styles_from_dict(data.get('styles', {})),
             keys=Keys.from_dict(data.get('keys', {})),
+            debug=data.get('debug', False),
         )
diff --git a/tail_jsonl/scripts.py b/tail_jsonl/scripts.py
index d47e6b7..db208f5 100644
--- a/tail_jsonl/scripts.py
+++ b/tail_jsonl/scripts.py
@@ -15,29 +15,35 @@
 from .config import Config
 
 
-def _load_config(config_path: str | None) -> Config:
+def _load_config(config_path: str | None, *, debug: bool = False) -> Config:
     """Return loaded specified configuration file."""
     user_config: dict = {}  # type: ignore[type-arg]
     if config_path:
         pth = Path(config_path).expanduser()
         user_config = tomllib.loads(pth.read_text(encoding='utf-8'))
-    return Config.from_dict(user_config)
+    config = Config.from_dict(user_config)
+    # CLI debug flag overrides config file
+    if debug:
+        config.debug = True
+    return config
 
 
 def start() -> None:  # pragma: no cover
     """CLI Entrypoint."""
-    # PLANNED: Add a flag (--debug & store_true) to print debugging information
-
     parser = argparse.ArgumentParser(description='Pipe JSONL Logs for pretty printing')
     parser.add_argument(
         '-v', '--version', action='version',
         version=f'%(prog)s {__version__}', help="Show program's version number and exit.",
     )
     parser.add_argument('--config-path', help='Path to a configuration file')
+    parser.add_argument(
+        '--debug', action='store_true',
+        help='Enable debug mode to show parsing details and error information',
+    )
     options = parser.parse_args(sys.argv[1:])
     sys.argv = sys.argv[:1]  # Remove CLI before calling fileinput
 
-    config = _load_config(options.config_path)
+    config = _load_config(options.config_path, debug=options.debug)
     console = Console()
     with fileinput.input() as _f:
         for line in _f:
diff --git a/tests/test_config.py b/tests/test_config.py
index 04c0836..141e643 100644
--- a/tests/test_config.py
+++ b/tests/test_config.py
@@ -12,4 +12,7 @@ def test_create_default_config():
 
     config = _load_config(config_path=str(example_config))
 
-    assert tomllib.loads(example_config.read_text(encoding='utf-8')) == asdict(config)
+    # Exclude 'debug' field as it's a runtime flag, not part of config file
+    config_dict = asdict(config)
+    config_dict.pop('debug', None)
+    assert tomllib.loads(example_config.read_text(encoding='utf-8')) == config_dict