QB Issue Resolution:
If it is for checks, try buying check stock and print them in the system. Then match them when they clear the bank. That works best for checks.
Resolution for Issue 'Why do I have to keep clicking Find Other Matching transactions???' available: Yes (Solved).
Source: Intuit Community forum.
Why do I have to keep clicking Find Other Matching transactions???: this issue or error code is a known issue in Quickbooks Online (QBO) and/or Quickbooks. Support for this issue is available either by self-service or paid support options. Experts are available to resolve your Quickbooks issue to ensure minimal downtime and continue running your business. First try to resolve the issue yourself by looking for a resolution described below. If it is a complex issue or you are unable to solve the issue, you may contact us by clicking here or by using other support options.Support for clicking Find
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Error Recovery for clicking Find [Canada]
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