diff --git a/.gitignore b/.gitignore
index 7520b7c..77ae426 100644
--- a/.gitignore
+++ b/.gitignore
@@ -5,3 +5,4 @@ data/
 prism-*
 tmp
 .VSCodeCounter/
+.image-digests
diff --git a/Makefile b/Makefile
index 6c51f06..f6fda73 100644
--- a/Makefile
+++ b/Makefile
@@ -53,17 +53,23 @@ check-updates:
 	@echo "=== Dockerfile base image updates ==="
 	@for image in $$(grep -E '^FROM ' Dockerfile | awk '{print $$2}' | grep -v 'AS'); do \
 		echo "Checking $$image..."; \
-		current_digest=$$(docker inspect --format='{{index .RepoDigests 0}}' $$image 2>/dev/null | cut -d@ -f2); \
-		docker pull -q $$image > /dev/null 2>&1; \
-		latest_digest=$$(docker inspect --format='{{index .RepoDigests 0}}' $$image 2>/dev/null | cut -d@ -f2); \
-		if [ -z "$$current_digest" ]; then \
-			echo "  $$image: pulled (no prior local image to compare)"; \
-		elif [ "$$current_digest" = "$$latest_digest" ]; then \
+		name=$$(echo $$image | cut -d: -f1); \
+		tag=$$(echo $$image | cut -d: -f2); \
+		digest=$$(curl -sf "https://hub.docker.com/v2/repositories/library/$$name/tags/$$tag" | jq -r '.digest // empty'); \
+		if [ -z "$$digest" ]; then \
+			echo "  $$image: could not fetch digest (offline or image not found)"; \
+			continue; \
+		fi; \
+		cache_key=$$(echo $$image | tr ':/' '--'); \
+		stored=$$(grep "^$$cache_key=" .image-digests 2>/dev/null | cut -d= -f2); \
+		if [ -z "$$stored" ]; then \
+			echo "$$cache_key=$$digest" >> .image-digests; \
+			echo "  $$image: digest saved for future comparisons"; \
+		elif [ "$$stored" = "$$digest" ]; then \
 			echo "  $$image: up to date"; \
 		else \
-			echo "  $$image: UPDATE AVAILABLE"; \
-			echo "    local:  $$current_digest"; \
-			echo "    latest: $$latest_digest"; \
+			sed -i "s|^$$cache_key=.*|$$cache_key=$$digest|" .image-digests; \
+			echo "  $$image: UPDATE AVAILABLE (image content has changed, consider rebuilding)"; \
 		fi; \
 	done
 
diff --git a/go.mod b/go.mod
index afcc9a5..982ffb9 100644
--- a/go.mod
+++ b/go.mod
@@ -8,9 +8,9 @@ require (
 	github.com/go-chi/chi/v5 v5.2.5
 	github.com/go-chi/httprate v0.15.0
 	github.com/joho/godotenv v1.5.1
-	github.com/mymmrac/telego v1.7.0
+	github.com/mymmrac/telego v1.8.0
 	golang.org/x/crypto v0.49.0
-	modernc.org/sqlite v1.48.0
+	modernc.org/sqlite v1.48.1
 )
 
 require (
diff --git a/go.sum b/go.sum
index 72d6dab..48e544c 100644
--- a/go.sum
+++ b/go.sum
@@ -47,8 +47,8 @@ github.com/klauspost/cpuid/v2 v2.3.0 h1:S4CRMLnYUhGeDFDqkGriYKdfoFlDnMtqTiI/sFzh
 github.com/klauspost/cpuid/v2 v2.3.0/go.mod h1:hqwkgyIinND0mEev00jJYCxPNVRVXFQeu1XKlok6oO0=
 github.com/mattn/go-isatty v0.0.20 h1:xfD0iDuEKnDkl03q4limB+vH+GxLEtL/jb4xVJSWWEY=
 github.com/mattn/go-isatty v0.0.20/go.mod h1:W+V8PltTTMOvKvAeJH7IuucS94S2C6jfK/D7dTCTo3Y=
-github.com/mymmrac/telego v1.7.0 h1:yRO/l00tFGG4nY66ufUKb4ARqv7qx9+LsjQv/b0NEyo=
-github.com/mymmrac/telego v1.7.0/go.mod h1:pdLV346EgVuq7Xrh3kMggeBiazeHhsdEoK0RTEOPXRM=
+github.com/mymmrac/telego v1.8.0 h1:EvIprWo9Cn0MHgumvvqNXPAXO1yJj3pu2cdCCeDxbow=
+github.com/mymmrac/telego v1.8.0/go.mod h1:pdLV346EgVuq7Xrh3kMggeBiazeHhsdEoK0RTEOPXRM=
 github.com/ncruces/go-strftime v1.0.0 h1:HMFp8mLCTPp341M/ZnA4qaf7ZlsbTc+miZjCLOFAw7w=
 github.com/ncruces/go-strftime v1.0.0/go.mod h1:Fwc5htZGVVkseilnfgOVb9mKy6w1naJmn9CehxcKcls=
 github.com/pmezard/go-difflib v1.0.0 h1:4DBwDE0NGyQoBHbLQYPwSUPoCMWR5BEzIk/f1lZbAQM=
@@ -183,8 +183,8 @@ modernc.org/opt v0.1.4 h1:2kNGMRiUjrp4LcaPuLY2PzUfqM/w9N23quVwhKt5Qm8=
 modernc.org/opt v0.1.4/go.mod h1:03fq9lsNfvkYSfxrfUhZCWPk1lm4cq4N+Bh//bEtgns=
 modernc.org/sortutil v1.2.1 h1:+xyoGf15mM3NMlPDnFqrteY07klSFxLElE2PVuWIJ7w=
 modernc.org/sortutil v1.2.1/go.mod h1:7ZI3a3REbai7gzCLcotuw9AC4VZVpYMjDzETGsSMqJE=
-modernc.org/sqlite v1.48.0 h1:ElZyLop3Q2mHYk5IFPPXADejZrlHu7APbpB0sF78bq4=
-modernc.org/sqlite v1.48.0/go.mod h1:hWjRO6Tj/5Ik8ieqxQybiEOUXy0NJFNp2tpvVpKlvig=
+modernc.org/sqlite v1.48.1 h1:S85iToyU6cgeojybE2XJlSbcsvcWkQ6qqNXJHtW5hWA=
+modernc.org/sqlite v1.48.1/go.mod h1:hWjRO6Tj/5Ik8ieqxQybiEOUXy0NJFNp2tpvVpKlvig=
 modernc.org/strutil v1.2.1 h1:UneZBkQA+DX2Rp35KcM69cSsNES9ly8mQWD71HKlOA0=
 modernc.org/strutil v1.2.1/go.mod h1:EHkiggD70koQxjVdSBM3JKM7k6L0FbGE5eymy9i3B9A=
 modernc.org/token v1.1.0 h1:Xl7Ap9dKaEs5kLoOQeQmPWevfnk/DM5qcLcYlA8ys6Y=