diff --git a/awk/generate_sidebar.awk b/awk/generate_sidebar.awk
index 8088264..8a5be5a 100644
--- a/awk/generate_sidebar.awk
+++ b/awk/generate_sidebar.awk
@@ -43,8 +43,47 @@ function get_title(path, default_title,   full_path, line, title, in_fm) {
     return default_title
 }
 
+function get_priority(path,   full_path, line, prio, in_fm) {
+    full_path = src "/" path
+    if (path !~ /\.md$/) {
+        full_path = full_path "/index.md"
+    }
 
-function compare_paths(p1, p2,    parts1, parts2, n1, n2, i, name1, name2, lname1, lname2, w1, w2) {
+    prio = ""
+    in_fm = 0
+    while ((getline line < full_path) > 0) {
+        if (line ~ /^---[[:space:]]*$/) {
+            if (in_fm == 0) {
+                in_fm = 1
+                continue
+            } else {
+                break
+            }
+        }
+        if (in_fm) {
+            if (line ~ /^[[:space:]]*priority[[:space:]]*=/) {
+                sub(/^[[:space:]]*priority[[:space:]]*=[[:space:]]*/, "", line)
+                if (line ~ /^".*"$/) {
+                    prio = substr(line, 2, length(line) - 2)
+                } else if (line ~ /^'.*'$/) {
+                    prio = substr(line, 2, length(line) - 2)
+                } else {
+                    prio = line
+                }
+                break
+            }
+        } else {
+            break
+        }
+    }
+    close(full_path)
+
+    if (prio != "" && prio + 0 == prio) return prio + 0
+    return 0
+}
+
+
+function compare_paths(p1, p2,    parts1, parts2, n1, n2, i, k, name1, name2, lname1, lname2, pr1, pr2, dir1, dir2, ent1, ent2) {
     n1 = split(p1, parts1, "/")
     n2 = split(p2, parts2, "/")
     for (i = 1; i <= n1 && i <= n2; i++) {
@@ -58,14 +97,36 @@ function compare_paths(p1, p2,    parts1, parts2, n1, n2, i, name1, name2, lname
         if (lname1 == "index" && i == n1 && lname2 != "index") return -1
         if (lname2 == "index" && i == n2 && lname1 != "index") return 1
 
-        w1 = (lname1 in custom_order ? custom_order[lname1] : 999999)
-        w2 = (lname2 in custom_order ? custom_order[lname2] : 999999)
+        if (lname1 != lname2) {
+            dir1 = ""
+            dir2 = ""
+            for (k = 1; k < i; k++) {
+                dir1 = (dir1 == "" ? parts1[k] : dir1 "/" parts1[k])
+                dir2 = (dir2 == "" ? parts2[k] : dir2 "/" parts2[k])
+            }
 
-        if (w1 < w2) return -1
-        if (w1 > w2) return 1
+            if (i == n1) {
+                pr1 = get_priority(p1)
+            } else {
+                ent1 = (dir1 == "" ? name1 : dir1 "/" name1)
+                pr1 = get_priority(ent1)
+            }
 
-        if (lname1 < lname2) return -1
-        if (lname1 > lname2) return 1
+            if (i == n2) {
+                pr2 = get_priority(p2)
+            } else {
+                ent2 = (dir2 == "" ? name2 : dir2 "/" name2)
+                pr2 = get_priority(ent2)
+            }
+
+            if (pr1 > 0 || pr2 > 0) {
+                if (pr1 < pr2) return -1
+                if (pr1 > pr2) return 1
+            }
+
+            if (lname1 < lname2) return -1
+            if (lname1 > lname2) return 1
+        }
     }
     if (n1 < n2) return -1
     if (n1 > n2) return 1
@@ -76,7 +137,6 @@ BEGIN {
     src = ENVIRON["AWK_SRC"]
     single_file_index = ENVIRON["AWK_SINGLE_FILE_INDEX"]
     flatten = ENVIRON["AWK_FLATTEN"]
-    order = ENVIRON["AWK_ORDER"]
     home_name = ENVIRON["AWK_HOME_NAME"]
     show_home_in_nav = ENVIRON["AWK_SHOW_HOME_IN_NAV"]
     dinfo = ENVIRON["AWK_DINFO"]
@@ -87,16 +147,6 @@ BEGIN {
             d_dirs[dparts[1]] = dparts[3]
         }
     }
-
-    n_order = split(order, oparts, ",")
-    for (i = 1; i <= n_order; i++) {
-        name = oparts[i]
-        sub(/^[[:space:]]*/, "", name)
-        sub(/[[:space:]]*$/, "", name)
-        if (name != "") {
-            custom_order[tolower(name)] = i
-        }
-    }
 }
 
 {
diff --git a/lib/builder.sh b/lib/builder.sh
index e200870..73cd4e6 100644
--- a/lib/builder.sh
+++ b/lib/builder.sh
@@ -170,10 +170,17 @@ eval "find \"$src\" \( $IGNORE_ARGS \) -prune -o -type d -print" | sort | while
                         label="$p_date $p_time"
                     fi
                 fi
-                if [ "$is_post_entry" = "true" ]; then
-                    sort_key="${p_date} ${p_time}"
+                if [ -n "$fm_priority" ]; then
+                    prio_val="$fm_priority"
                 else
-                    sort_key="$name"
+                    prio_val="0"
+                fi
+                if [ "$is_post_entry" = "true" ]; then
+                    prio_key=$(printf '%05d' "$prio_val")
+                    sort_key="${prio_key} ${p_date} ${p_time}"
+                else
+                    prio_key=$(printf '%05d' "$((99999 - prio_val))")
+                    sort_key="${prio_key} $name"
                 fi
                 echo "${sort_key}|- [$label](${name%.md}.html)|$name|${name%.md}.html" >> "$temp_entries"
             else
diff --git a/lib/config.sh b/lib/config.sh
index a8a33db..edef9c8 100644
--- a/lib/config.sh
+++ b/lib/config.sh
@@ -5,7 +5,6 @@ draft_by_default = false
 dir_indexes = true
 single_file_index = true
 flatten = false
-order = ""
 home_name = "Home"
 show_home_in_nav = true
 nav_links = ""
@@ -67,7 +66,6 @@ footer="made with <a href=\"https://kewt.krzak.org\">kewt</a>"
 dir_indexes="true"
 single_file_index="true"
 flatten="false"
-order=""
 home_name="Home"
 show_home_in_nav="true"
 nav_links=""
@@ -127,7 +125,6 @@ load_config() {
             dir_indexes) dir_indexes="$val" ;;
             single_file_index) single_file_index="$val" ;;
             flatten) flatten="$val" ;;
-            order) order="$val" ;;
             home_name) home_name="$val" ;;
             show_home_in_nav) show_home_in_nav="$val" ;;
             nav_links) nav_links="$val" ;;
diff --git a/lib/generator.sh b/lib/generator.sh
index b521b4c..61bcde3 100644
--- a/lib/generator.sh
+++ b/lib/generator.sh
@@ -8,7 +8,7 @@ generate_nav() {
     if [ -n "$posts_dir" ] && [ -d "$1/$posts_dir" ]; then
         find_cmd="$find_cmd && echo \"$1/$posts_dir/index.md\""
     fi
-    eval "$find_cmd" | sort -u | AWK_SRC="$1" AWK_SINGLE_FILE_INDEX="$single_file_index" AWK_FLATTEN="$flatten" AWK_ORDER="$order" AWK_HOME_NAME="$home_name" AWK_SHOW_HOME_IN_NAV="$show_home_in_nav" AWK_DINFO="$dinfo" awk -f "$awk_dir/generate_sidebar.awk"
+    eval "$find_cmd" | sort -u | AWK_SRC="$1" AWK_SINGLE_FILE_INDEX="$single_file_index" AWK_FLATTEN="$flatten" AWK_HOME_NAME="$home_name" AWK_SHOW_HOME_IN_NAV="$show_home_in_nav" AWK_DINFO="$dinfo" awk -f "$awk_dir/generate_sidebar.awk"
 }
 escape_html_text() {
     printf '%s' "$1" | sed \
@@ -34,6 +34,7 @@ parse_frontmatter() {
     fm_description=""
     fm_content_warning=""
     fm_tags=""
+    fm_priority=""
     while IFS='=' read -r _fk _fv; do
         case "$_fk" in
             title) fm_title="$_fv" ;;
@@ -42,6 +43,7 @@ parse_frontmatter() {
             description) fm_description="$_fv" ;;
             content_warning) fm_content_warning="$_fv" ;;
             tags) fm_tags="$_fv" ;;
+            priority) fm_priority="$_fv" ;;
         esac
     done < "$_fm_out"
     rm -f "$_fm_out"
diff --git a/site/depths/deeper depths/deeper deeper depths/the deepest depths/blobfish/blobfish.md b/site/depths/deeper depths/deeper deeper depths/the deepest depths/blobfish/blobfish.md
index 5ab61b2..202f650 100644
--- a/site/depths/deeper depths/deeper deeper depths/the deepest depths/blobfish/blobfish.md	
+++ b/site/depths/deeper depths/deeper deeper depths/the deepest depths/blobfish/blobfish.md	
@@ -1,3 +1,6 @@
+---
+priority = 0
+---
 # Hello!
 
 ![the greatest drawing of a blobfish in the world](blobfish.bmp)
diff --git a/site/depths/index.md b/site/depths/index.md
index 6468175..a2c9285 100644
--- a/site/depths/index.md
+++ b/site/depths/index.md
@@ -1,3 +1,6 @@
+---
+priority = 2
+---
 # Depths
 
 This is a custom index for a directory
diff --git a/site/docs/configuration.md b/site/docs/configuration.md
index 38f8493..b9bae1d 100644
--- a/site/docs/configuration.md
+++ b/site/docs/configuration.md
@@ -1,5 +1,6 @@
 ---
 title = "Configuration"
+priority = 2
 ---
 # Configuration
 
@@ -13,7 +14,6 @@ draft_by_default = false
 dir_indexes = true
 single_file_index = true
 flatten = false
-order = ""
 home_name = "Home"
 show_home_in_nav = true
 nav_links = ""
@@ -49,7 +49,6 @@ include_cw_pages_in_search = false
 - `dir_indexes` - generate directory index pages when missing `index.md`
 - `single_file_index` - if a directory has one markdown file and no `index.md`, use that file as `index.html`
 - `flatten` - flatten sidebar directory levels
-- `order` - comma separated file/directory name list to order the sidebar (alphabetical by default)
 - `home_name` - text for the home link in navigation (default: "Home")
 - `show_home_in_nav` - show home link in navigation (default: true)
 - `nav_links` - comma separated extra nav links, as bare URLs or Markdown links like `[Label](https://example.com)`
diff --git a/site/docs/embeds.md b/site/docs/embeds.md
index ec90b87..4da6d68 100644
--- a/site/docs/embeds.md
+++ b/site/docs/embeds.md
@@ -1,5 +1,6 @@
 ---
 title = "Embeds"
+priority = 5
 ---
 # Embeds
 
diff --git a/site/docs/frontmatter.md b/site/docs/frontmatter.md
index 12d707f..7b47859 100644
--- a/site/docs/frontmatter.md
+++ b/site/docs/frontmatter.md
@@ -1,5 +1,6 @@
 ---
 title = "Frontmatter"
+priority = 4
 ---
 # Frontmatter
 
@@ -12,6 +13,7 @@ date = "2026-03-23 11:32"
 draft = false
 description = "A short page summary"
 tags = "example, tutorial"
+priority = 10
 ---
 ```
 - `title` - overrides the page title, post name in index links, and RSS `<title>`.
@@ -20,3 +22,4 @@ tags = "example, tutorial"
 - `description` - page description, used for Open Graph `og:description` meta tag.
 - `tags` - comma separated list of tags. Used for tag index generation when `generate_tags` is enabled in `site.conf`.
 - `content_warning` - if set, creates an interstitial warning page that the user must click through. If set to `true` uses a generic warning, otherwise uses your string.
+- `priority` - numeric value for ordering. Lower values sort first in the sidebar and directory indexes. Falls back to alphabetical/date ordering when not set or when items share the same priority.
diff --git a/site/docs/index.md b/site/docs/index.md
index 5e68b9f..753a448 100644
--- a/site/docs/index.md
+++ b/site/docs/index.md
@@ -1,5 +1,6 @@
 ---
 title = "Documentation"
+priority = 0
 ---
 # Documentation
 
diff --git a/site/docs/installation.md b/site/docs/installation.md
index b419092..2ba6281 100644
--- a/site/docs/installation.md
+++ b/site/docs/installation.md
@@ -1,5 +1,6 @@
 ---
 title = "Installation"
+priority = 0
 ---
 # Installation
 
diff --git a/site/docs/markdown.md b/site/docs/markdown.md
index 4a125d5..b7055b5 100644
--- a/site/docs/markdown.md
+++ b/site/docs/markdown.md
@@ -1,5 +1,6 @@
 ---
 title = "Markdown Extensions"
+priority = 7
 ---
 # Markdown Extensions
 
diff --git a/site/docs/quickstart.md b/site/docs/quickstart.md
index 3962abb..922e035 100644
--- a/site/docs/quickstart.md
+++ b/site/docs/quickstart.md
@@ -1,5 +1,6 @@
 ---
 title = "Quickstart"
+priority = 1
 ---
 # Quickstart
 
diff --git a/site/docs/templates.md b/site/docs/templates.md
index 55ff0e8..0a22280 100644
--- a/site/docs/templates.md
+++ b/site/docs/templates.md
@@ -1,5 +1,6 @@
 ---
 title = "Templates"
+priority = 8
 ---
 # Templates
 
diff --git a/site/docs/theming.md b/site/docs/theming.md
index 4fa0372..423c26b 100644
--- a/site/docs/theming.md
+++ b/site/docs/theming.md
@@ -1,5 +1,6 @@
 ---
 title = "Theming"
+priority = 6
 ---
 # Theming
 
diff --git a/site/docs/usage.md b/site/docs/usage.md
index 3774e80..05e3114 100644
--- a/site/docs/usage.md
+++ b/site/docs/usage.md
@@ -1,5 +1,6 @@
 ---
 title = "Usage"
+priority = 3
 ---
 # Usage
 
diff --git a/site/heaven/index.md b/site/heaven/index.md
index 00054b5..eef62d2 100644
--- a/site/heaven/index.md
+++ b/site/heaven/index.md
@@ -1,5 +1,6 @@
 ---
 title = "Heaven"
+priority = 3
 content_warning = "This page may contain CSS"
 ---
 # Heaven
diff --git a/site/index.md b/site/index.md
index d5a3078..819d263 100644
--- a/site/index.md
+++ b/site/index.md
@@ -1,3 +1,7 @@
+---
+title = "Home"
+priority = 0
+---
 # _kewt_
 ### Pronounced "cute"
 
@@ -14,7 +18,7 @@ It's meant to be a static site generator, like _[kew](https://github.com/uint23/
 ## Features
 
 - No dependencies
-- Frontmatter support (title, date, draft, description)
+- Frontmatter support (title, date, draft, description, priority)
 - Supports many embed types
 - Automatic css variable replacement for older browsers
 - Automatic inlining and embedding of many filetypes with `\![link]` or `\![alt](link)`
diff --git a/site/site.conf b/site/site.conf
index 1a2aa84..c304eee 100644
--- a/site/site.conf
+++ b/site/site.conf
@@ -9,7 +9,6 @@ display_logo = false
 display_title = true
 logo_as_favicon = false
 favicon = "favicon.ico"
-order = "Home, docs, depths, heaven"
 home_name = "Home"
 show_home_in_nav = true
 nav_links = ""