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 5e40a22ad..46fd38643 100644
--- a/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationUtil.tsx
+++ b/apps/roam/src/components/canvas/DiscourseRelationShape/DiscourseRelationUtil.tsx
@@ -65,6 +65,7 @@ import {
 } from "./helpers";
 import { createReifiedRelation } from "~/utils/createReifiedBlock";
 import { getStoredRelationsEnabled } from "~/utils/storedRelations";
+import type { DiscourseRelation } from "~/utils/getDiscourseRelations";
 import { discourseContext, isPageUid } from "~/components/canvas/Tldraw";
 import getPageUidByPageTitle from "roamjs-components/queries/getPageUidByPageTitle";
 
@@ -624,41 +625,77 @@ 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;
+
+        // Check all relations with the same label for a match
+        const {
+          isDirect,
+          isReverse,
+          matchingRelation: foundRelation,
+        } = this.checkConnectionTypeAcrossLabel(
+          relation.label,
+          sourceNodeType,
+          targetNodeType,
+        );
+        const matchingRelation = foundRelation ?? relation;
+
+        if (!isDirect && !isReverse) {
+          const validTargets = this.getValidTargetTypes(
+            relation.label,
+            sourceNodeType,
+          );
+          const uniqueTargetTexts = validTargets.map(
+            (t) => discourseContext.nodes[t]?.text || t,
           );
           return deleteAndWarn(
             `Target node must be of type ${uniqueTargetTexts.join(", ")}`,
           );
         }
-        if (arrow.type !== target.type) {
-          editor.updateShapes([{ id: arrow.id, type: target.type }]);
+
+        // If we found a matching relation with a different ID, switch to it
+        if (matchingRelation.id !== arrow.type) {
+          // Get bindings before updating the shape type
+          const existingBindings = editor.getBindingsFromShape(
+            arrow,
+            arrow.type,
+          );
+          // Update the shape type
+          editor.updateShapes([{ id: arrow.id, type: matchingRelation.id }]);
+          // Update bindings to use the new relation type
+          for (const binding of existingBindings) {
+            editor.updateBinding({
+              ...binding,
+              type: matchingRelation.id,
+            });
+          }
         }
         if (getStoredRelationsEnabled()) {
           const sourceAsDNS = asDiscourseNodeShape(source, editor);
           const targetAsDNS = asDiscourseNodeShape(target, editor);
 
-          if (sourceAsDNS && targetAsDNS)
+          if (sourceAsDNS && targetAsDNS) {
+            const isOriginal = isDirect;
             await createReifiedRelation({
-              sourceUid: sourceAsDNS.props.uid,
-              destinationUid: targetAsDNS.props.uid,
-              relationBlockUid: relation.id,
+              sourceUid: isOriginal
+                ? sourceAsDNS.props.uid
+                : targetAsDNS.props.uid,
+              destinationUid: isOriginal
+                ? targetAsDNS.props.uid
+                : sourceAsDNS.props.uid,
+              relationBlockUid: matchingRelation.id,
             });
-          else {
+          } else {
             void internalError({
               error: "attempt to create a relation between non discourse nodes",
               type: "Canvas create relation",
             });
           }
         } else {
-          const { triples, label: relationLabel } = relation;
-          const isOriginal = arrow.props.text === relationLabel;
+          const { triples } = matchingRelation;
+          const isOriginal = isDirect;
+
           const newTriples = triples
             .map((t) => {
               if (/is a/i.test(t[1])) {
@@ -845,6 +882,33 @@ 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) {
+              removeArrowBinding(this.editor, shape, handleId);
+              update.props![handleId] = { x: handle.x, y: handle.y };
+              return update;
+            }
+          }
+        }
+
         // we've got a target! the handle is being dragged over a shape, bind to it
 
         const targetGeometry = this.editor.getShapeGeometry(target);
@@ -921,6 +985,42 @@ 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 { isReverse, matchingRelation } =
+                this.checkConnectionTypeAcrossLabel(
+                  relation.label,
+                  startNodeType,
+                  endNodeType,
+                );
+
+              const effectiveRelation = matchingRelation ?? relation;
+
+              const newText =
+                isReverse && effectiveRelation.complement
+                  ? effectiveRelation.complement
+                  : effectiveRelation.label;
+
+              if (shape.props.text !== newText) {
+                update.props = update.props || {};
+                update.props.text = newText;
+              }
+            }
+          }
+        }
+
         if (
           newBindings.start &&
           newBindings.end &&
@@ -1601,6 +1701,79 @@ 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 };
+  }
+
+  checkConnectionTypeAcrossLabel(
+    label: string,
+    sourceNodeType: string,
+    targetNodeType: string,
+  ): {
+    isDirect: boolean;
+    isReverse: boolean;
+    matchingRelation: DiscourseRelation | null;
+  } {
+    const relationsWithLabel = discourseContext.relations[label];
+    if (!relationsWithLabel) {
+      return { isDirect: false, isReverse: false, matchingRelation: null };
+    }
+
+    for (const rel of relationsWithLabel) {
+      const { isDirect, isReverse } = this.checkConnectionType(
+        rel,
+        sourceNodeType,
+        targetNodeType,
+      );
+      if (isDirect || isReverse) {
+        return { isDirect, isReverse, matchingRelation: rel };
+      }
+    }
+
+    return { isDirect: false, isReverse: false, matchingRelation: null };
+  }
+
+  getValidTargetTypes(label: string, sourceNodeType: string): string[] {
+    const relationsWithLabel = discourseContext.relations[label];
+    if (!relationsWithLabel) return [];
+
+    const targets = new Set<string>();
+    for (const rel of relationsWithLabel) {
+      if (rel.source === sourceNodeType) targets.add(rel.destination);
+      if (rel.destination === sourceNodeType) targets.add(rel.source);
+    }
+    return [...targets];
+  }
+
+  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.checkConnectionTypeAcrossLabel(
+      relation.label,
+      sourceNodeType,
+      targetNodeType,
+    );
+    return isDirect || isReverse;
+  }
+
   component(shape: DiscourseRelationShape) {
     // eslint-disable-next-line react-hooks/rules-of-hooks
     // const theme = useDefaultColorTheme();