diff --git a/.github/actions/build-electron/action.yml b/.github/actions/build-electron/action.yml
index 1e84179595..abc038a6a1 100644
--- a/.github/actions/build-electron/action.yml
+++ b/.github/actions/build-electron/action.yml
@@ -80,6 +80,14 @@ runs:
       wget -q "https://github.com/AppImage/appimagetool/releases/download/continuous/appimagetool-${APPIMAGETOOL_ARCH}.AppImage" -O /usr/local/bin/appimagetool
       chmod +x /usr/local/bin/appimagetool
 
+  # See the equivalent step in build-server: substitute an addon built against an
+  # older glibc for better-sqlite3's bundled prebuild, before electron-forge
+  # packages node_modules/better-sqlite3 into the app.
+  - name: Rebuild better-sqlite3 against an older glibc
+    if: ${{ inputs.os == 'linux' }}
+    shell: ${{ inputs.shell }}
+    run: bash scripts/build-portable-better-sqlite3.sh ${{ inputs.arch }}
+
   - name: Update build info
     shell: ${{ inputs.shell }}
     run: pnpm run chore:update-build-info
diff --git a/.github/actions/build-server/action.yml b/.github/actions/build-server/action.yml
index efdb0728f5..6c4f984a18 100644
--- a/.github/actions/build-server/action.yml
+++ b/.github/actions/build-server/action.yml
@@ -17,6 +17,14 @@ runs:
   - name: Install dependencies
     shell: bash
     run: pnpm install --frozen-lockfile
+  # better-sqlite3 v13's bundled prebuilds are linked against a much newer glibc
+  # than the assets previous releases shipped, which would drop distributions we
+  # still support. Recompile against an older one before the build copies
+  # node_modules/better-sqlite3 into dist/.
+  - name: Rebuild better-sqlite3 against an older glibc
+    if: ${{ inputs.os == 'linux' }}
+    shell: bash
+    run: bash scripts/build-portable-better-sqlite3.sh ${{ inputs.arch }}
   - name: Run Linux server build
     env:
       MATRIX_ARCH: ${{ inputs.arch }}
diff --git a/scripts/build-portable-better-sqlite3.sh b/scripts/build-portable-better-sqlite3.sh
new file mode 100755
index 0000000000..60a86fa275
--- /dev/null
+++ b/scripts/build-portable-better-sqlite3.sh
@@ -0,0 +1,215 @@
+#!/usr/bin/env bash
+#
+# Recompile better-sqlite3 from source inside an older container, so the addon we
+# ship targets an older glibc/libstdc++ than upstream's bundled prebuilds.
+#
+# better-sqlite3 v13 ships N-API prebuilds for every platform. They are portable
+# across runtimes, but they are linked against whatever toolchain upstream builds
+# on -- currently glibc 2.34/GCC 11 (x64) and glibc 2.38/GCC 13 (arm64). That is
+# far newer than the assets previous Trilium releases shipped (glibc 2.29), and
+# it drops distributions we still support (Debian 12 / Raspberry Pi OS bookworm
+# on arm64, Ubuntu 20.04 / Debian 11 on x64). Nothing in better-sqlite3 needs a
+# newer glibc; the floor is purely an artifact of the build host, so we rebuild
+# on an older one and substitute the result.
+#
+# Usage: ./build-portable-better-sqlite3.sh [arch]
+#   arch: x64 or arm64 (default: the host's arch)
+#
+# Environment variables:
+#   BS3_BUILD_IMAGE     container image to compile in (default: node:22-bullseye).
+#                       The image's glibc sets the floor, so this is the knob that
+#                       decides which distributions we support:
+#                         node:22-bullseye (glibc 2.31, GCC 10) -> Debian 11+,
+#                           Ubuntu 20.04+; restores roughly the v0.104.1 floor.
+#                         node:24-bookworm (glibc 2.36, GCC 12) -> Debian 12+,
+#                           Ubuntu 22.04+, RHEL 9+.
+#                       The Node version is irrelevant to the result: the addon is
+#                       N-API, so it does not bind to the runtime it was built on.
+#                       g++/make come from buildpack-deps in the full (non-slim)
+#                       images; python3 does not, so it is apt-installed when
+#                       missing (which also makes -slim images usable).
+#   BS3_DOCKER          command used to reach Docker (default: docker). Set to
+#                       "sudo docker" where the daemon needs root.
+#   BS3_NO_DOCKER       if set, compile directly on the host instead of in a
+#                       container. Only useful for testing the mechanism; the
+#                       resulting floor is the host's, not the image's.
+#   BS3_PRUNE_PREBUILDS if set, delete the prebuilds for every other platform
+#                       from the shipped copies (saves ~15 MB per artifact).
+#
+# Must run after `pnpm install` and before any `*:build` task, since the build
+# scripts copy node_modules/better-sqlite3 into dist/ verbatim.
+
+set -euo pipefail
+
+ARCH="${1:-$(node -p 'process.arch')}"
+IMAGE="${BS3_BUILD_IMAGE:-node:22-bullseye}"
+
+case "$ARCH" in
+    x64|arm64) ;;
+    *) echo "Unsupported architecture: $ARCH (expected x64 or arm64)" >&2; exit 1 ;;
+esac
+
+TARGET="linux-$ARCH"
+REPO_ROOT="$(cd "$(dirname "$0")/.." && pwd)"
+cd "$REPO_ROOT"
+
+# Report the highest versioned symbol an addon references from each of the two
+# libraries whose version floors we care about. These are the numbers a host has
+# to satisfy in order to load it.
+floors() {
+    local f="$1"
+    if [ ! -f "$f" ] || ! command -v objdump > /dev/null; then
+        echo "(unavailable)"
+        return
+    fi
+    local glibc glibcxx
+    glibc="$(objdump -T "$f" | grep -o 'GLIBC_[0-9.]*' | sort -uV | tail -1)"
+    glibcxx="$(objdump -T "$f" | grep -o 'GLIBCXX_[0-9.]*' | sort -uV | tail -1)"
+    echo "${glibc:-none} / ${glibcxx:-none}"
+}
+
+# nodeLinker is "hoisted", so each package that depends on better-sqlite3 gets its
+# own directory tree rather than a symlink into a single store location. The build
+# scripts resolve <app>/node_modules first and fall back to the root, so every
+# copy has to receive the rebuilt binary.
+mapfile -t BS3_DIRS < <(find . -type d -name better-sqlite3 -path '*/node_modules/better-sqlite3' -not -path './*/dist/*' -not -path './node_modules/@types/*' | sort)
+if [ "${#BS3_DIRS[@]}" -eq 0 ]; then
+    echo "No better-sqlite3 installation found -- run 'pnpm install' first." >&2
+    exit 1
+fi
+
+BUILD_DIR="${BS3_DIRS[0]}"
+echo "Compiling in:  $BUILD_DIR"
+echo "Target:        $TARGET"
+echo "Before:        $(floors "$BUILD_DIR/prebuilds/$TARGET.node" 2>/dev/null || echo "(upstream prebuild)")"
+
+# force_build is required: better-sqlite3's binding.gyp resolves both of its
+# targets to `type: none` whenever a prebuild for the host exists, so an ordinary
+# node-gyp run emits a stamp file and no addon at all.
+BUILD_SCRIPT='
+set -eu
+bs3_dir="$1"
+repo_root="$2"
+owner="${3:-}"
+
+# buildpack-deps (the base of the full node images) provides g++ and make but not
+# python3, which node-gyp requires. Install whatever is missing rather than
+# assuming, so both full and -slim images work.
+missing=""
+for tool in python3 make g++; do
+    command -v "$tool" > /dev/null 2>&1 || missing="$missing $tool"
+done
+if [ -n "$missing" ] && [ -n "$owner" ]; then
+    echo "Installing build tools:$missing"
+    apt_opts=""
+    # A Debian suite stops being served from deb.debian.org once it goes EOL and
+    # moves to archive.debian.org (bullseye: 2026-08-31). We deliberately build on
+    # an old release to keep the glibc floor low -- see the header -- so handle the
+    # move rather than being broken by it. Archived Release files are expired by
+    # definition, hence Check-Valid-Until=false.
+    if ! apt-get update -qq 2> /dev/null; then
+        echo "deb.debian.org did not serve this suite; retrying via archive.debian.org"
+        for src in /etc/apt/sources.list /etc/apt/sources.list.d/*.list /etc/apt/sources.list.d/*.sources; do
+            [ -f "$src" ] || continue
+            sed -i -e "s|deb\.debian\.org|archive.debian.org|g" \
+                   -e "s|security\.debian\.org|archive.debian.org|g" "$src"
+        done
+        apt_opts="-o Acquire::Check-Valid-Until=false"
+        # Tolerate a non-zero exit: -updates/-backports are absent from the
+        # archive, but the main suite still indexes, which is all we need.
+        apt-get $apt_opts update -qq || true
+    fi
+    apt-get install -y -qq --no-install-recommends $apt_opts $missing
+elif [ -n "$missing" ]; then
+    echo "Missing build tools:$missing" >&2
+    exit 1
+fi
+
+# Prefer the node-gyp bundled with npm (present in the official node images).
+# Fall back to the workspace copy, which nixpkgs-style slim runtimes need since
+# they strip node-gyp out of npm.
+node_gyp="${BS3_NODE_GYP:-}"
+if [ -z "$node_gyp" ]; then
+    for candidate in \
+        "$(npm root -g)/npm/node_modules/node-gyp/bin/node-gyp.js" \
+        "$repo_root/node_modules/.bin/node-gyp"; do
+        if [ -f "$candidate" ]; then node_gyp="$candidate"; break; fi
+    done
+fi
+if [ -z "$node_gyp" ]; then
+    echo "No node-gyp found. Set BS3_NODE_GYP to point at one." >&2
+    exit 1
+fi
+echo "Using node-gyp: $node_gyp"
+
+cd "$bs3_dir"
+rm -rf build
+export npm_config_force_build=1
+node "$node_gyp" rebuild --release
+
+# The container runs as root so it can apt-install python3, which would otherwise
+# leave root-owned files in the bind-mounted workspace.
+if [ -n "$owner" ]; then
+    chown -R "$owner" "$bs3_dir"
+fi
+'
+
+if [ -n "${BS3_NO_DOCKER:-}" ]; then
+    echo "Building on the host (BS3_NO_DOCKER set) -- floors will be the host's."
+    bash -c "$BUILD_SCRIPT" _ "$BUILD_DIR" "$REPO_ROOT"
+else
+    read -r -a DOCKER_CMD <<< "${BS3_DOCKER:-docker}"
+    if ! "${DOCKER_CMD[@]}" info > /dev/null 2>&1; then
+        echo "Cannot reach the Docker daemon via '${BS3_DOCKER:-docker}'." >&2
+        echo "If Docker needs root on this machine, re-run with:" >&2
+        echo "  BS3_DOCKER='sudo docker' $0 $ARCH" >&2
+        exit 1
+    fi
+    # Be explicit about the target platform: a no-op on CI, where the arm64 job
+    # runs on a native arm64 runner, but it lets the arm64 build be reproduced
+    # locally on an x64 machine that has binfmt/qemu registered.
+    DOCKER_PLATFORM="linux/$([ "$ARCH" = "x64" ] && echo amd64 || echo arm64)"
+    echo "Building in:   $IMAGE ($DOCKER_PLATFORM, via ${DOCKER_CMD[*]})"
+    "${DOCKER_CMD[@]}" run --rm \
+        --platform "$DOCKER_PLATFORM" \
+        -e npm_config_devdir=/tmp/.node-gyp \
+        -e "BS3_NODE_GYP=${BS3_NODE_GYP:-}" \
+        -v "$REPO_ROOT:/repo" \
+        -w /repo \
+        "$IMAGE" \
+        bash -c "$BUILD_SCRIPT" _ "/repo/${BUILD_DIR#./}" /repo "$(id -u):$(id -g)"
+fi
+
+COMPILED="$BUILD_DIR/build/Release/better_sqlite3.node"
+if [ ! -f "$COMPILED" ]; then
+    echo "Compile produced no addon at $COMPILED (force_build did not take effect?)" >&2
+    exit 1
+fi
+
+# Substitute the compiled addon for the upstream prebuild in every copy. Replace
+# via rename rather than writing in place: these files are hardlinks into the
+# pnpm store, and an in-place write would mutate the store for every project on
+# the machine.
+for dir in "${BS3_DIRS[@]}"; do
+    dest="$dir/prebuilds/$TARGET.node"
+    mkdir -p "$dir/prebuilds"
+    cp "$COMPILED" "$dest.tmp"
+    mv -f "$dest.tmp" "$dest"
+
+    if [ -n "${BS3_PRUNE_PREBUILDS:-}" ]; then
+        find "$dir/prebuilds" -name '*.node' ! -name "$TARGET.node" -delete
+    fi
+    echo "Installed:     $dest"
+done
+
+echo "After:         $(floors "$COMPILED")"
+
+# Prove the substituted binary actually loads and can execute a query, so a
+# silently broken artifact can't reach the release.
+node -e '
+const Database = require("better-sqlite3");
+const db = new Database(":memory:");
+const { v } = db.prepare("select sqlite_version() v").get();
+db.close();
+console.log("Verified:      loads, SQLite " + v);
+'