diff --git a/e2e/playwright/point-click.spec.ts b/e2e/playwright/point-click.spec.ts
index 76fbc60c1..35ab4fcc5 100644
--- a/e2e/playwright/point-click.spec.ts
+++ b/e2e/playwright/point-click.spec.ts
@@ -1078,7 +1078,7 @@ sketch002 = startSketchOn('XZ')
     await page.waitForTimeout(500)
     await cmdBar.progressCmdBar()
     await expect(
-      page.getByText('Unable to sweep with the provided selection')
+      page.getByText('Unable to sweep with the current selection. Reason:')
     ).toBeVisible()
   })
 })
@@ -1846,7 +1846,7 @@ sweep001 = sweep({ path = sketch002 }, sketch001)
     await page.waitForTimeout(500)
     await cmdBar.progressCmdBar()
     await expect(
-      page.getByText('Unable to shell with the provided selection')
+      page.getByText('Unable to shell with the current selection. Reason:')
     ).toBeVisible()
     await page.waitForTimeout(1000)
   })
diff --git a/src/lang/std/engineConnection.ts b/src/lang/std/engineConnection.ts
index 35fbe2b87..9ce37c119 100644
--- a/src/lang/std/engineConnection.ts
+++ b/src/lang/std/engineConnection.ts
@@ -1999,7 +1999,7 @@ export class EngineCommandManager extends EventTarget {
       .catch((e) => {
         // TODO: Previously was never caught, we are not rejecting these pendingCommands but this needs to be handled at some point.
         /*noop*/
-        return null
+        return e
       })
   }
   /**
diff --git a/src/lib/commandBarConfigs/validators.test.ts b/src/lib/commandBarConfigs/validators.test.ts
new file mode 100644
index 000000000..4862ab5a6
--- /dev/null
+++ b/src/lib/commandBarConfigs/validators.test.ts
@@ -0,0 +1,19 @@
+import { parseEngineErrorMessage } from './validators'
+
+describe('parseEngineErrorMessage', () => {
+  it('takes an engine error string and parses its json message', () => {
+    const engineError =
+      'engine error: [{"error_code":"internal_engine","message":"Trajectory curve must be G1 continuous (with continuous tangents)"}]'
+    const message = parseEngineErrorMessage(engineError)
+    expect(message).toEqual(
+      'Trajectory curve must be G1 continuous (with continuous tangents)'
+    )
+  })
+
+  it('retuns undefined on strings with different formats', () => {
+    const s1 = 'engine error: []'
+    const s2 = 'blabla'
+    expect(parseEngineErrorMessage(s1)).toBeUndefined()
+    expect(parseEngineErrorMessage(s2)).toBeUndefined()
+  })
+})
diff --git a/src/lib/commandBarConfigs/validators.ts b/src/lib/commandBarConfigs/validators.ts
index 2d87294aa..f478e584e 100644
--- a/src/lib/commandBarConfigs/validators.ts
+++ b/src/lib/commandBarConfigs/validators.ts
@@ -3,6 +3,7 @@ import { engineCommandManager } from 'lib/singletons'
 import { uuidv4 } from 'lib/utils'
 import { CommandBarContext } from 'machines/commandBarMachine'
 import { Selections } from 'lib/selections'
+import { ApiError_type } from '@kittycad/lib/dist/types/src/models'
 
 export const disableDryRunWithRetry = async (numberOfRetries = 3) => {
   for (let tries = 0; tries < numberOfRetries; tries++) {
@@ -46,6 +47,20 @@ function isSelections(selections: unknown): selections is Selections {
   )
 }
 
+export function parseEngineErrorMessage(engineError: string) {
+  const parts = engineError.split('engine error: ')
+  if (parts.length < 2) {
+    return undefined
+  }
+
+  const errors = JSON.parse(parts[1]) as ApiError_type[]
+  if (!errors[0]) {
+    return undefined
+  }
+
+  return errors[0].message
+}
+
 export const revolveAxisValidator = async ({
   data,
   context,
@@ -83,7 +98,7 @@ export const revolveAxisValidator = async ({
     value: 360,
   }
 
-  const revolveAboutEdgeCommand = async () => {
+  const command = async () => {
     return await engineCommandManager.sendSceneCommand({
       type: 'modeling_cmd_req',
       cmd_id: uuidv4(),
@@ -96,13 +111,13 @@ export const revolveAxisValidator = async ({
       },
     })
   }
-  const attemptRevolve = await dryRunWrapper(revolveAboutEdgeCommand)
-  if (attemptRevolve?.success) {
+  const result = await dryRunWrapper(command)
+  if (result?.success) {
     return true
-  } else {
-    // return error message for the toast
-    return 'Unable to revolve with selected edge'
   }
+
+  const reason = parseEngineErrorMessage(result) || 'unknown'
+  return `Unable to revolve with the current selection. Reason: ${reason}`
 }
 
 export const loftValidator = async ({
@@ -128,7 +143,7 @@ export const loftValidator = async ({
     return 'Unable to loft, selection contains less than two solid2ds'
   }
 
-  const loftCommand = async () => {
+  const command = async () => {
     // TODO: check what to do with these
     const DEFAULT_V_DEGREE = 2
     const DEFAULT_TOLERANCE = 2
@@ -145,13 +160,13 @@ export const loftValidator = async ({
       },
     })
   }
-  const attempt = await dryRunWrapper(loftCommand)
-  if (attempt?.success) {
+  const result = await dryRunWrapper(command)
+  if (result?.success) {
     return true
-  } else {
-    // return error message for the toast
-    return 'Unable to loft with selected sketches'
   }
+
+  const reason = parseEngineErrorMessage(result) || 'unknown'
+  return `Unable to loft with the current selection. Reason: ${reason}`
 }
 
 export const shellValidator = async ({
@@ -180,7 +195,7 @@ export const shellValidator = async ({
     return "Unable to shell, couldn't find the solid"
   }
 
-  const shellCommand = async () => {
+  const command = async () => {
     // TODO: figure out something better than an arbitrarily small value
     const DEFAULT_THICKNESS: Models['LengthUnit_type'] = 1e-9
     const DEFAULT_HOLLOW = false
@@ -200,12 +215,13 @@ export const shellValidator = async ({
     })
   }
 
-  const attemptShell = await dryRunWrapper(shellCommand)
-  if (attemptShell?.success) {
+  const result = await dryRunWrapper(command)
+  if (result?.success) {
     return true
   }
 
-  return 'Unable to shell with the provided selection'
+  const reason = parseEngineErrorMessage(result) || 'unknown'
+  return `Unable to shell with the current selection. Reason: ${reason}`
 }
 
 export const sweepValidator = async ({
@@ -241,7 +257,7 @@ export const sweepValidator = async ({
   }
   const target = targetArtifact.pathId
 
-  const sweepCommand = async () => {
+  const command = async () => {
     // TODO: second look on defaults here
     const DEFAULT_TOLERANCE: Models['LengthUnit_type'] = 1e-7
     const DEFAULT_SECTIONAL = false
@@ -261,10 +277,11 @@ export const sweepValidator = async ({
     })
   }
 
-  const attemptSweep = await dryRunWrapper(sweepCommand)
-  if (attemptSweep?.success) {
+  const result = await dryRunWrapper(command)
+  if (result?.success) {
     return true
   }
 
-  return 'Unable to sweep with the provided selection'
+  const reason = parseEngineErrorMessage(result) || 'unknown'
+  return `Unable to sweep with the current selection. Reason: ${reason}`
 }