diff --git a/app/Search/Options/TagSearchOption.php b/app/Search/Options/TagSearchOption.php
index e61c55ae4..dd2803db4 100644
--- a/app/Search/Options/TagSearchOption.php
+++ b/app/Search/Options/TagSearchOption.php
@@ -4,8 +4,34 @@ namespace BookStack\Search\Options;
 
 class TagSearchOption extends SearchOption
 {
+    /**
+     * Acceptable operators to be used within a tag search option.
+     *
+     * @var string[]
+     */
+    protected array $queryOperators = ['<=', '>=', '=', '<', '>', 'like', '!='];
+
     public function toString(): string
     {
         return ($this->negated ? '-' : '') . "[{$this->value}]";
     }
+
+    /**
+     * @return array{name: string, operator: string, value: string}
+     */
+    public function getParts(): array
+    {
+        $operatorRegex = implode('|', array_map(fn($op) => preg_quote($op), $this->queryOperators));
+        preg_match('/^(.*?)((' . $operatorRegex . ')(.*?))?$/', $this->value, $tagSplit);
+
+        $extractedOperator = count($tagSplit) > 2 ? $tagSplit[3] : '';
+        $tagOperator = in_array($extractedOperator, $this->queryOperators) ? $extractedOperator : '=';
+        $tagValue = count($tagSplit) > 3 ? $tagSplit[4] : '';
+
+        return [
+            'name' => $tagSplit[1],
+            'operator' => $tagOperator,
+            'value' => $tagValue,
+        ];
+    }
 }
diff --git a/app/Search/SearchOptionSet.php b/app/Search/SearchOptionSet.php
index 467dc9f5a..f421abe2c 100644
--- a/app/Search/SearchOptionSet.php
+++ b/app/Search/SearchOptionSet.php
@@ -4,10 +4,13 @@ namespace BookStack\Search;
 
 use BookStack\Search\Options\SearchOption;
 
+/**
+ * @template T of SearchOption
+ */
 class SearchOptionSet
 {
     /**
-     * @var SearchOption[]
+     * @var T[]
      */
     protected array $options = [];
 
@@ -52,7 +55,7 @@ class SearchOptionSet
     }
 
     /**
-     * @return SearchOption[]
+     * @return T[]
      */
     public function all(): array
     {
@@ -60,7 +63,7 @@ class SearchOptionSet
     }
 
     /**
-     * @return SearchOption[]
+     * @return T[]
      */
     public function negated(): array
     {
diff --git a/app/Search/SearchOptions.php b/app/Search/SearchOptions.php
index 98f731ee7..e362a8a01 100644
--- a/app/Search/SearchOptions.php
+++ b/app/Search/SearchOptions.php
@@ -11,9 +11,13 @@ use Illuminate\Http\Request;
 
 class SearchOptions
 {
+    /** @var SearchOptionSet<TermSearchOption> */
     public SearchOptionSet $searches;
+    /** @var SearchOptionSet<ExactSearchOption> */
     public SearchOptionSet $exacts;
+    /** @var SearchOptionSet<TagSearchOption> */
     public SearchOptionSet $tags;
+    /** @var SearchOptionSet<FilterSearchOption> */
     public SearchOptionSet $filters;
 
     public function __construct()
diff --git a/app/Search/SearchRunner.php b/app/Search/SearchRunner.php
index 855140508..265b9eecc 100644
--- a/app/Search/SearchRunner.php
+++ b/app/Search/SearchRunner.php
@@ -7,6 +7,7 @@ use BookStack\Entities\Models\Entity;
 use BookStack\Entities\Models\Page;
 use BookStack\Entities\Queries\EntityQueries;
 use BookStack\Permissions\PermissionApplicator;
+use BookStack\Search\Options\TagSearchOption;
 use BookStack\Users\Models\User;
 use Illuminate\Database\Connection;
 use Illuminate\Database\Eloquent\Builder as EloquentBuilder;
@@ -16,31 +17,21 @@ use Illuminate\Database\Query\Builder;
 use Illuminate\Support\Collection;
 use Illuminate\Support\Facades\DB;
 use Illuminate\Support\Str;
-use SplObjectStorage;
+use WeakMap;
 
 class SearchRunner
 {
-    /**
-     * Acceptable operators to be used in a query.
-     *
-     * @var string[]
-     */
-    protected array $queryOperators = ['<=', '>=', '=', '<', '>', 'like', '!='];
-
     /**
      * Retain a cache of score adjusted terms for specific search options.
-     * From PHP>=8 this can be made into a WeakMap instead.
-     *
-     * @var SplObjectStorage
      */
-    protected $termAdjustmentCache;
+    protected WeakMap $termAdjustmentCache;
 
     public function __construct(
         protected EntityProvider $entityProvider,
         protected PermissionApplicator $permissions,
         protected EntityQueries $entityQueries,
     ) {
-        $this->termAdjustmentCache = new SplObjectStorage();
+        $this->termAdjustmentCache = new WeakMap();
     }
 
     /**
@@ -163,24 +154,26 @@ class SearchRunner
         $this->applyTermSearch($entityQuery, $searchOpts, $entityType);
 
         // Handle exact term matching
-        foreach ($searchOpts->exacts->toValueArray() as $inputTerm) {
-            $entityQuery->where(function (EloquentBuilder $query) use ($inputTerm, $entityModelInstance) {
-                $inputTerm = str_replace('\\', '\\\\', $inputTerm);
+        foreach ($searchOpts->exacts->all() as $exact) {
+            $filter = function (EloquentBuilder $query) use ($exact, $entityModelInstance) {
+                $inputTerm = str_replace('\\', '\\\\', $exact->value);
                 $query->where('name', 'like', '%' . $inputTerm . '%')
                     ->orWhere($entityModelInstance->textField, 'like', '%' . $inputTerm . '%');
-            });
+            };
+
+            $exact->negated ? $entityQuery->whereNot($filter) : $entityQuery->where($filter);
         }
 
         // Handle tag searches
-        foreach ($searchOpts->tags->toValueArray() as $inputTerm) {
-            $this->applyTagSearch($entityQuery, $inputTerm);
+        foreach ($searchOpts->tags->all() as $tagOption) {
+            $this->applyTagSearch($entityQuery, $tagOption);
         }
 
         // Handle filters
-        foreach ($searchOpts->filters->toValueMap() as $filterTerm => $filterValue) {
-            $functionName = Str::camel('filter_' . $filterTerm);
+        foreach ($searchOpts->filters->all() as $filterOption) {
+            $functionName = Str::camel('filter_' . $filterOption->getKey());
             if (method_exists($this, $functionName)) {
-                $this->$functionName($entityQuery, $entityModelInstance, $filterValue);
+                $this->$functionName($entityQuery, $entityModelInstance, $filterOption->value, $filterOption->negated);
             }
         }
 
@@ -312,179 +305,165 @@ class SearchRunner
     }
 
     /**
-     * Get the available query operators as a regex escaped list.
+     * Apply a tag search term onto an entity query.
      */
-    protected function getRegexEscapedOperators(): string
+    protected function applyTagSearch(EloquentBuilder $query, TagSearchOption $option): void
     {
-        $escapedOperators = [];
-        foreach ($this->queryOperators as $operator) {
-            $escapedOperators[] = preg_quote($operator);
-        }
+        $filter = function (EloquentBuilder $query) use ($option): void {
+            $tagParts = $option->getParts();
+            if (empty($tagParts['operator']) || empty($tagParts['value'])) {
+                $query->where('name', '=', $tagParts['name']);
+                return;
+            }
 
-        return implode('|', $escapedOperators);
+            if (!empty($tagParts['name'])) {
+                $query->where('name', '=', $tagParts['name']);
+            }
+
+            if (is_numeric($tagParts['value']) && $tagParts['operator'] !== 'like') {
+                // We have to do a raw sql query for this since otherwise PDO will quote the value and MySQL will
+                // search the value as a string which prevents being able to do number-based operations
+                // on the tag values. We ensure it has a numeric value and then cast it just to be sure.
+                /** @var Connection $connection */
+                $connection = $query->getConnection();
+                $quotedValue = (float) trim($connection->getPdo()->quote($tagParts['value']), "'");
+                $query->whereRaw("value {$tagParts['operator']} {$quotedValue}");
+            } else if ($tagParts['operator'] === 'like') {
+                $query->where('value', $tagParts['operator'], str_replace('\\', '\\\\', $tagParts['value']));
+            } else {
+                $query->where('value', $tagParts['operator'], $tagParts['value']);
+            }
+        };
+
+        $option->negated ? $query->whereDoesntHave('tags', $filter) : $query->whereHas('tags', $filter);
     }
 
-    /**
-     * Apply a tag search term onto a entity query.
-     */
-    protected function applyTagSearch(EloquentBuilder $query, string $tagTerm): EloquentBuilder
+    protected function applyNegatableWhere(EloquentBuilder $query, bool $negated, string $column, string $operator, mixed $value): void
     {
-        preg_match('/^(.*?)((' . $this->getRegexEscapedOperators() . ')(.*?))?$/', $tagTerm, $tagSplit);
-        $query->whereHas('tags', function (EloquentBuilder $query) use ($tagSplit) {
-            $tagName = $tagSplit[1];
-            $tagOperator = count($tagSplit) > 2 ? $tagSplit[3] : '';
-            $tagValue = count($tagSplit) > 3 ? $tagSplit[4] : '';
-            $validOperator = in_array($tagOperator, $this->queryOperators);
-            if (!empty($tagOperator) && !empty($tagValue) && $validOperator) {
-                if (!empty($tagName)) {
-                    $query->where('name', '=', $tagName);
-                }
-                if (is_numeric($tagValue) && $tagOperator !== 'like') {
-                    // We have to do a raw sql query for this since otherwise PDO will quote the value and MySQL will
-                    // search the value as a string which prevents being able to do number-based operations
-                    // on the tag values. We ensure it has a numeric value and then cast it just to be sure.
-                    /** @var Connection $connection */
-                    $connection = $query->getConnection();
-                    $tagValue = (float) trim($connection->getPdo()->quote($tagValue), "'");
-                    $query->whereRaw("value {$tagOperator} {$tagValue}");
-                } else {
-                    if ($tagOperator === 'like') {
-                        $tagValue = str_replace('\\', '\\\\', $tagValue);
-                    }
-                    $query->where('value', $tagOperator, $tagValue);
-                }
-            } else {
-                $query->where('name', '=', $tagName);
-            }
-        });
-
-        return $query;
+        if ($negated) {
+            $query->whereNot($column, $operator, $value);
+        } else {
+            $query->where($column, $operator, $value);
+        }
     }
 
     /**
      * Custom entity search filters.
      */
-    protected function filterUpdatedAfter(EloquentBuilder $query, Entity $model, $input): void
+    protected function filterUpdatedAfter(EloquentBuilder $query, Entity $model, string $input, bool $negated): void
     {
-        try {
-            $date = date_create($input);
-            $query->where('updated_at', '>=', $date);
-        } catch (\Exception $e) {
-        }
+        $date = date_create($input);
+        $this->applyNegatableWhere($query, $negated, 'updated_at', '>=', $date);
     }
 
-    protected function filterUpdatedBefore(EloquentBuilder $query, Entity $model, $input): void
+    protected function filterUpdatedBefore(EloquentBuilder $query, Entity $model, string $input, bool $negated): void
     {
-        try {
-            $date = date_create($input);
-            $query->where('updated_at', '<', $date);
-        } catch (\Exception $e) {
-        }
+        $date = date_create($input);
+        $this->applyNegatableWhere($query, $negated, 'updated_at', '<', $date);
     }
 
-    protected function filterCreatedAfter(EloquentBuilder $query, Entity $model, $input): void
+    protected function filterCreatedAfter(EloquentBuilder $query, Entity $model, string $input, bool $negated): void
     {
-        try {
-            $date = date_create($input);
-            $query->where('created_at', '>=', $date);
-        } catch (\Exception $e) {
-        }
+        $date = date_create($input);
+        $this->applyNegatableWhere($query, $negated, 'created_at', '>=', $date);
     }
 
-    protected function filterCreatedBefore(EloquentBuilder $query, Entity $model, $input)
+    protected function filterCreatedBefore(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
-        try {
-            $date = date_create($input);
-            $query->where('created_at', '<', $date);
-        } catch (\Exception $e) {
-        }
+        $date = date_create($input);
+        $this->applyNegatableWhere($query, $negated, 'created_at', '<', $date);
     }
 
-    protected function filterCreatedBy(EloquentBuilder $query, Entity $model, $input)
+    protected function filterCreatedBy(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
         $userSlug = $input === 'me' ? user()->slug : trim($input);
         $user = User::query()->where('slug', '=', $userSlug)->first(['id']);
         if ($user) {
-            $query->where('created_by', '=', $user->id);
+            $this->applyNegatableWhere($query, $negated, 'created_by', '=', $user->id);
         }
     }
 
-    protected function filterUpdatedBy(EloquentBuilder $query, Entity $model, $input)
+    protected function filterUpdatedBy(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
         $userSlug = $input === 'me' ? user()->slug : trim($input);
         $user = User::query()->where('slug', '=', $userSlug)->first(['id']);
         if ($user) {
-            $query->where('updated_by', '=', $user->id);
+            $this->applyNegatableWhere($query, $negated, 'updated_by', '=', $user->id);
         }
     }
 
-    protected function filterOwnedBy(EloquentBuilder $query, Entity $model, $input)
+    protected function filterOwnedBy(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
         $userSlug = $input === 'me' ? user()->slug : trim($input);
         $user = User::query()->where('slug', '=', $userSlug)->first(['id']);
         if ($user) {
-            $query->where('owned_by', '=', $user->id);
+            $this->applyNegatableWhere($query, $negated, 'owned_by', '=', $user->id);
         }
     }
 
-    protected function filterInName(EloquentBuilder $query, Entity $model, $input)
+    protected function filterInName(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
-        $query->where('name', 'like', '%' . $input . '%');
+        $this->applyNegatableWhere($query, $negated, 'name', 'like', '%' . $input . '%');
     }
 
-    protected function filterInTitle(EloquentBuilder $query, Entity $model, $input)
+    protected function filterInTitle(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
-        $this->filterInName($query, $model, $input);
+        $this->filterInName($query, $model, $input, $negated);
     }
 
-    protected function filterInBody(EloquentBuilder $query, Entity $model, $input)
+    protected function filterInBody(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
-        $query->where($model->textField, 'like', '%' . $input . '%');
+        $this->applyNegatableWhere($query, $negated, $model->textField, 'like', '%' . $input . '%');
     }
 
-    protected function filterIsRestricted(EloquentBuilder $query, Entity $model, $input)
+    protected function filterIsRestricted(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
-        $query->whereHas('permissions');
+        $negated ? $query->whereDoesntHave('permissions') : $query->whereHas('permissions');
     }
 
-    protected function filterViewedByMe(EloquentBuilder $query, Entity $model, $input)
+    protected function filterViewedByMe(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
-        $query->whereHas('views', function ($query) {
+        $filter = function ($query) {
             $query->where('user_id', '=', user()->id);
-        });
+        };
+
+        $negated ? $query->whereDoesntHave('views', $filter) : $query->whereHas('views', $filter);
     }
 
-    protected function filterNotViewedByMe(EloquentBuilder $query, Entity $model, $input)
+    protected function filterNotViewedByMe(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
-        $query->whereDoesntHave('views', function ($query) {
+        $filter = function ($query) {
             $query->where('user_id', '=', user()->id);
-        });
+        };
+
+        $negated ? $query->whereHas('views', $filter) : $query->whereDoesntHave('views', $filter);
     }
 
-    protected function filterIsTemplate(EloquentBuilder $query, Entity $model, $input)
+    protected function filterIsTemplate(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
         if ($model instanceof Page) {
-            $query->where('template', '=', true);
+            $this->applyNegatableWhere($query, $negated, 'template', '=', true);
         }
     }
 
-    protected function filterSortBy(EloquentBuilder $query, Entity $model, $input)
+    protected function filterSortBy(EloquentBuilder $query, Entity $model, string $input, bool $negated)
     {
         $functionName = Str::camel('sort_by_' . $input);
         if (method_exists($this, $functionName)) {
-            $this->$functionName($query, $model);
+            $this->$functionName($query, $model, $negated);
         }
     }
 
     /**
      * Sorting filter options.
      */
-    protected function sortByLastCommented(EloquentBuilder $query, Entity $model)
+    protected function sortByLastCommented(EloquentBuilder $query, Entity $model, bool $negated)
     {
         $commentsTable = DB::getTablePrefix() . 'comments';
         $morphClass = str_replace('\\', '\\\\', $model->getMorphClass());
         $commentQuery = DB::raw('(SELECT c1.entity_id, c1.entity_type, c1.created_at as last_commented FROM ' . $commentsTable . ' c1 LEFT JOIN ' . $commentsTable . ' c2 ON (c1.entity_id = c2.entity_id AND c1.entity_type = c2.entity_type AND c1.created_at < c2.created_at) WHERE c1.entity_type = \'' . $morphClass . '\' AND c2.created_at IS NULL) as comments');
 
-        $query->join($commentQuery, $model->getTable() . '.id', '=', 'comments.entity_id')->orderBy('last_commented', 'desc');
+        $query->join($commentQuery, $model->getTable() . '.id', '=', 'comments.entity_id')
+            ->orderBy('last_commented', $negated ? 'asc' : 'desc');
     }
 }
diff --git a/tests/Entity/EntitySearchTest.php b/tests/Entity/EntitySearchTest.php
index c3e959345..bb1021a67 100644
--- a/tests/Entity/EntitySearchTest.php
+++ b/tests/Entity/EntitySearchTest.php
@@ -118,6 +118,32 @@ class EntitySearchTest extends TestCase
         $exactSearchB->assertStatus(200)->assertDontSee($page->name);
     }
 
+    public function test_negated_searches()
+    {
+        $page = $this->entities->newPage(['name' => 'My new test negation page', 'html' => '<p>An angry tortoise wore trumpeted plimsoles</p>']);
+        $page->tags()->saveMany([new Tag(['name' => 'DonkCount', 'value' => '500'])]);
+        $page->created_by = $this->users->admin()->id;
+        $page->save();
+
+        $editor = $this->users->editor();
+        $this->actingAs($editor);
+
+        $exactSearch = $this->get('/search?term=' . urlencode('negation -"tortoise"'));
+        $exactSearch->assertStatus(200)->assertDontSeeText($page->name);
+
+        $tagSearchA = $this->get('/search?term=' . urlencode('negation [DonkCount=500]'));
+        $tagSearchA->assertStatus(200)->assertSeeText($page->name);
+        $tagSearchB = $this->get('/search?term=' . urlencode('negation -[DonkCount=500]'));
+        $tagSearchB->assertStatus(200)->assertDontSeeText($page->name);
+
+        $filterSearchA = $this->get('/search?term=' . urlencode('negation -{created_by:me}'));
+        $filterSearchA->assertStatus(200)->assertSeeText($page->name);
+        $page->created_by = $editor->id;
+        $page->save();
+        $filterSearchB = $this->get('/search?term=' . urlencode('negation -{created_by:me}'));
+        $filterSearchB->assertStatus(200)->assertDontSeeText($page->name);
+    }
+
     public function test_search_terms_with_delimiters_are_converted_to_exact_matches()
     {
         $this->asEditor();