diff --git a/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationTool.tsx b/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationTool.tsx
index 3e809406b..8c068c2bc 100644
--- a/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationTool.tsx
+++ b/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationTool.tsx
@@ -363,14 +363,17 @@ export const createAllRelationShapeTools = (
           );
 
           const relation = discourseContext.relations[name].find(
-            (r) => r.source === target?.type,
+            (r) => r.source === target?.type || r.destination === target?.type,
           );
           if (relation) {
             this.shapeType = relation.id;
           } else {
-            const acceptableTypes = discourseContext.relations[name].map(
-              (r) => discourseContext.nodes[r.source].text,
-            );
+            const acceptableTypes = discourseContext.relations[name]
+              .flatMap((r) => [
+                discourseContext.nodes[r.source]?.text,
+                discourseContext.nodes[r.destination]?.text,
+              ])
+              .filter(Boolean);
             const uniqueTypes = [...new Set(acceptableTypes)];
             this.cancelAndWarn(
               `Starting node must be one of ${uniqueTypes.join(", ")}`,
diff --git a/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationUtil.tsx b/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationUtil.tsx
index 198e75916..23d1dbf8a 100644
--- a/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationUtil.tsx
+++ b/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationUtil.tsx
@@ -537,14 +537,30 @@ export const createAllRelationShapeUtils = (
         const relations = Object.values(discourseContext.relations).flat();
         const relation = relations.find((r) => r.id === arrow.type);
         if (!relation) return;
-        const possibleTargets = discourseContext.relations[relation.label]
-          .filter((r) => r.source === relation.source)
-          .map((r) => r.destination);
 
-        if (!possibleTargets.includes(target.type)) {
-          const uniqueTargets = [...new Set(possibleTargets)];
-          const uniqueTargetTexts = uniqueTargets.map(
-            (t) => discourseContext.nodes[t].text,
+        const sourceNodeType = source.type;
+        const targetNodeType = target.type;
+
+        const { isDirect, isReverse } = this.checkConnectionType(
+          relation,
+          sourceNodeType,
+          targetNodeType,
+        );
+
+        if (!isDirect && !isReverse) {
+          const possibleTargets = discourseContext.relations[relation.label]
+            .filter((r) => r.source === relation.source)
+            .map((r) => r.destination);
+          const possibleReverseTargets = discourseContext.relations[
+            relation.label
+          ]
+            .filter((r) => r.destination === relation.source)
+            .map((r) => r.source);
+          const allPossibleTargets = [
+            ...new Set([...possibleTargets, ...possibleReverseTargets]),
+          ];
+          const uniqueTargetTexts = allPossibleTargets.map(
+            (t) => discourseContext.nodes[t]?.text || t,
           );
           return deleteAndWarn(
             `Target node must be of type ${uniqueTargetTexts.join(", ")}`,
@@ -553,6 +569,7 @@ export const createAllRelationShapeUtils = (
         if (arrow.type !== target.type) {
           editor.updateShapes([{ id: arrow.id, type: target.type }]);
         }
+        arrow = editor.getShape(arrow.id) as DiscourseRelationShape;
         if (getSetting("use-reified-relations")) {
           const sourceAsDNS = asDiscourseNodeShape(source, editor);
           const targetAsDNS = asDiscourseNodeShape(target, editor);
@@ -572,8 +589,9 @@ export const createAllRelationShapeUtils = (
             }).catch(() => undefined);
           }
         } else {
-          const { triples, label: relationLabel } = relation;
-          const isOriginal = arrow.props.text === relationLabel;
+          const { triples } = relation;
+          const isOriginal = isDirect && !isReverse;
+
           const newTriples = triples
             .map((t) => {
               if (/is a/i.test(t[1])) {
@@ -756,6 +774,52 @@ export const createAllRelationShapeUtils = (
           return update;
         }
 
+        // Validate target node type compatibility before creating binding
+        if (
+          target.type !== "arrow" &&
+          otherBinding &&
+          target.id !== otherBinding.toId &&
+          (!currentBinding || target.id !== currentBinding.toId)
+        ) {
+          const sourceNodeId = otherBinding.toId;
+          const sourceNode = this.editor.getShape(sourceNodeId);
+          const targetNodeType = target.type;
+          const sourceNodeType = sourceNode?.type;
+
+          if (sourceNodeType && targetNodeType && shape.type) {
+            const isValidConnection = this.isValidNodeConnection(
+              sourceNodeType,
+              targetNodeType,
+              shape.type,
+            );
+
+            if (!isValidConnection) {
+              const sourceNodeTypeText =
+                discourseContext.nodes[sourceNodeType]?.text || sourceNodeType;
+              const targetNodeTypeText =
+                discourseContext.nodes[targetNodeType]?.text || targetNodeType;
+              const relations = Object.values(
+                discourseContext.relations,
+              ).flat();
+              const relation = relations.find((r) => r.id === shape.type);
+              const relationLabel = relation?.label || shape.type;
+
+              const errorMessage = `Cannot connect "${sourceNodeTypeText}" to "${targetNodeTypeText}" with "${relationLabel}" relation`;
+              dispatchToastEvent({
+                id: `tldraw-invalid-connection-${shape.id}`,
+                title: "Invalid Connection",
+                description: errorMessage,
+                severity: "error",
+              });
+
+              removeArrowBinding(this.editor, shape, handleId);
+              update.props![handleId] = { x: handle.x, y: handle.y };
+              this.editor.deleteShapes([shape.id]);
+              return update;
+            }
+          }
+        }
+
         // we've got a target! the handle is being dragged over a shape, bind to it
 
         const targetGeometry = this.editor.getShapeGeometry(target);
@@ -832,6 +896,37 @@ export const createAllRelationShapeUtils = (
         this.editor.setHintingShapes([target.id]);
 
         const newBindings = getArrowBindings(this.editor, shape);
+
+        // Check if both ends are bound and determine the correct text based on direction
+        if (newBindings.start && newBindings.end) {
+          const relations = Object.values(discourseContext.relations).flat();
+          const relation = relations.find((r) => r.id === shape.type);
+
+          if (relation) {
+            const startNode = this.editor.getShape(newBindings.start.toId);
+            const endNode = this.editor.getShape(newBindings.end.toId);
+
+            if (startNode && endNode) {
+              const startNodeType = startNode.type;
+              const endNodeType = endNode.type;
+
+              const { isDirect, isReverse } = this.checkConnectionType(
+                relation,
+                startNodeType,
+                endNodeType,
+              );
+
+              const newText =
+                isReverse && !isDirect ? relation.complement : relation.label;
+
+              if (shape.props.text !== newText) {
+                update.props = update.props || {};
+                update.props.text = newText;
+              }
+            }
+          }
+        }
+
         if (
           newBindings.start &&
           newBindings.end &&
@@ -1454,6 +1549,40 @@ export class BaseDiscourseRelationUtil extends ShapeUtil<DiscourseRelationShape>
     ];
   }
 
+  checkConnectionType(
+    relation: { source: string; destination: string },
+    sourceNodeType: string,
+    targetNodeType: string,
+  ): { isDirect: boolean; isReverse: boolean } {
+    const isDirect =
+      sourceNodeType === relation.source &&
+      targetNodeType === relation.destination;
+
+    const isReverse =
+      sourceNodeType === relation.destination &&
+      targetNodeType === relation.source;
+
+    return { isDirect, isReverse };
+  }
+
+  isValidNodeConnection(
+    sourceNodeType: string,
+    targetNodeType: string,
+    relationId: string,
+  ): boolean {
+    const relations = Object.values(discourseContext.relations).flat();
+    const relation = relations.find((r) => r.id === relationId);
+    if (!relation) return false;
+
+    const { isDirect, isReverse } = this.checkConnectionType(
+      relation,
+      sourceNodeType,
+      targetNodeType,
+    );
+
+    return isDirect || isReverse;
+  }
+
   component(shape: DiscourseRelationShape) {
     // eslint-disable-next-line react-hooks/rules-of-hooks
     // const theme = useDefaultColorTheme();