[Bug] Memories are ignored until explicitly re-requested, defeating their purpose

Bug Description
It frequently appears that the primary purpose of "memories" is for Claude to ignore them until such time as I ask it again to record a rule going forward, in which case it spots the existing memory and says "We already have that rule, I just ignored it." This is not a productive use of "memory" and is not in fact "memory" at all. "memories" should be remembered, not ignored. "Rules" that aren't followed, merely used to say "Oh, yes, I was supposed to do that and didn't" are not in any way productive.

Environment Info

• Platform: darwin
• Terminal: vscode
• Version: 2.1.278
• Feedback ID: dcf2bf4e-8542-44cf-9a4b-3f4950a593a5

Errors

[{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CfHaQpasjkdGemFZk6CEt\"}\n    at generate (/$bunfs/root/chunk-ctwtwgcv.js:11:14493)\n    at makeRequest (/$bunfs/root/chunk-ctwtwgcv.js:51:8033)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-09-22T01:03:04.528Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CfHabzk8AZcjbZutC49nT\"}\n    at generate (/$bunfs/root/chunk-ctwtwgcv.js:11:14493)\n    at makeRequest (/$bunfs/root/chunk-ctwtwgcv.js:51:8033)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-09-22T01:05:36.388Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CfHao85D51AkBtwWVJ3y2\"}\n    at generate (/$bunfs/root/chunk-ctwtwgcv.js:11:14493)\n    at makeRequest (/$bunfs/root/chunk-ctwtwgcv.js:51:8033)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-09-22T01:08:07.205Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CfHbYAmNjA6WsSAsrSHxQ\"}\n    at generate (/$bunfs/root/chunk-ctwtwgcv.js:11:14493)\n    at makeRequest (/$bunfs/root/chunk-ctwtwgcv.js:51:8033)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-09-22T01:17:51.411Z"},{"error":"Error: 500 {\"type\":\"error\",\"error\":{\"type\":\"api_error\",\"message\":\"Internal server error\"},\"request_id\":\"req_011CfHc2g9F4Pg5u29rgDkim\"}\n    at generate (/$bunfs/root/chunk-ctwtwgcv.js:11:14493)\n    at makeRequest (/$bunfs/root/chunk-ctwtwgcv.js:51:8033)\n    at processTicksAndRejections (native:7:39)","timestamp":"2026-09-22T01:24:18.447Z"}]