diff --git a/textproc/py-ocrmypdf/Makefile b/textproc/py-ocrmypdf/Makefile
index 2c5fb666c483..3f10735c9596 100644
--- a/textproc/py-ocrmypdf/Makefile
+++ b/textproc/py-ocrmypdf/Makefile
@@ -1,76 +1,76 @@
 PORTNAME=	ocrmypdf
-DISTVERSION=	14.3.0
+DISTVERSION=	14.4.0
 CATEGORIES=	textproc python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	kai@FreeBSD.org
 COMMENT=	Adds an OCR text layer to scanned PDF files
 WWW=		https://github.com/ocrmypdf/OCRmyPDF
 
 LICENSE=	MPL20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PY_SETUPTOOLS} \
 		${PYTHON_PKGNAMEPREFIX}setuptools_scm>=0:devel/py-setuptools_scm@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}coloredlogs>=14.0:devel/py-coloredlogs@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}deprecation>=2.1.0:devel/py-deprecation@${PY_FLAVOR} \
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}deprecation>=2.1.0:devel/py-deprecation@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}img2pdf>=0.3.0:graphics/py-img2pdf@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=20:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pillow>=8.2.0:graphics/py-pillow@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tqdm>=4:misc/py-tqdm@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}reportlab>=3.5.66:print/py-reportlab@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}rich>=13:textproc/py-rich@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pdfminer.six>=20201018:textproc/py-pdfminer.six@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pikepdf>=5.0.1:textproc/py-pikepdf@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pluggy>=0.13.0:devel/py-pluggy@${PY_FLAVOR} \
 		tesseract:graphics/tesseract
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}hypothesis>=6.0.0:devel/py-hypothesis@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-xdist>=2.2.0:devel/py-pytest-xdist@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}python-xmp-toolkit>=2.0.1:textproc/py-python-xmp-toolkit@${PY_FLAVOR}
 
 USES=		ghostscript:run python shebangfix
 USE_PYTHON=	autoplist concurrent pep517 pytest
 # Skip some checks as they yield wrong results if run with the root account
 PYTEST_IGNORED_TESTS=	test_chmod \
 			test_dev_null \
 			test_input_file_not_readable \
 			test_outputtype_none
 
 SHEBANG_FILES=	src/ocrmypdf/__main__.py \
 		src/ocrmypdf/hocrtransform.py \
 		src/ocrmypdf/pdfinfo/__init__.py
 
 TEST_ARGS=	-n ${MAKE_JOBS_NUMBER}
 TEST_ENV=	PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 
 NO_ARCH=	yes
 
 PLIST_FILES=	etc/bash_completion.d/ocrmypdf.bash share/fish/vendor_completions.d/ocrmypdf.fish
 
 OPTIONS_DEFINE=	PNGQUANT UNPAPER
 OPTIONS_DEFAULT=PNGQUANT UNPAPER
 
 PNGQUANT_DESC=	Optimizes the encoding of PNG-style images in PDFs
 UNPAPER_DESC=	Deskew and clean up pages before OCR processing
 
 PNGQUANT_RUN_DEPENDS=	pngquant:graphics/pngquant
 UNPAPER_RUN_DEPENDS=	unpaper:graphics/unpaper
 
 .include <bsd.port.pre.mk>
 
 .if ${PYTHON_REL} < 30900
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}importlib-resources>=5:devel/py-importlib-resources@${PY_FLAVOR}
 .endif
 
 .if ${PYTHON_REL} < 31000
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}typing-extensions>=4:devel/py-typing-extensions@${PY_FLAVOR}
 .endif
 
 post-install:
 	# Install shell completion files
 	@${MKDIR} ${STAGEDIR}${PREFIX}/etc/bash_completion.d ${STAGEDIR}${PREFIX}/share/fish/vendor_completions.d/
 	${INSTALL_DATA} ${WRKSRC}/misc/completion/ocrmypdf.bash ${STAGEDIR}${PREFIX}/etc/bash_completion.d/
 	${INSTALL_DATA} ${WRKSRC}/misc/completion/ocrmypdf.fish ${STAGEDIR}${PREFIX}/share/fish/vendor_completions.d/
 
 .include <bsd.port.post.mk>
diff --git a/textproc/py-ocrmypdf/distinfo b/textproc/py-ocrmypdf/distinfo
index 66af08e045ca..8c42b702660d 100644
--- a/textproc/py-ocrmypdf/distinfo
+++ b/textproc/py-ocrmypdf/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1687855125
-SHA256 (ocrmypdf-14.3.0.tar.gz) = faa221f53771a6679ad541307a0e66e11d298a33a2840cf1908a6a46f8315ede
-SIZE (ocrmypdf-14.3.0.tar.gz) = 6529259
+TIMESTAMP = 1692336408
+SHA256 (ocrmypdf-14.4.0.tar.gz) = bd6fcc813cc9766768058687cf94efe3403993244b19c51771617403858c692d
+SIZE (ocrmypdf-14.4.0.tar.gz) = 6530803