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Navigating tax questions for long term bitcoin investors

Taxes and Security Concerns | Users Weigh in on DCA Risks

By

Chen Wei

Jul 22, 2025, 09:43 AM

Edited By

Alice Wong

3 minutes reading time

A person analyzing Bitcoin transactions and tax documents on a laptop, with charts and graphs in the background.
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As daily dollar-cost averaging (DCA) in crypto gains traction, concerns about security and tax obligations are rising. With custodial exchanges facing scrutiny, individuals are questioning how to manage their investments and maintain accurate records.

Some people emphasize the potential risks of using platforms like Strike, which have custodial control over assets. "You donโ€™t own it, so if they disappear, your money is at risk," one commenter noted. This highlights the fear many have when relying on third-party services to hold their crypto investments.

Record Keeping Beyond Custodians

In the event of an exchange shutting down, users are advised to keep their own records. Many suggest storing transaction detailsโ€”like dates, amounts, and feesโ€”securely. As one user put it, "You are responsible for your records. Make them yourself."

Interestingly, people are considering various methods to safeguard their cost basis histories. Some propose saving yearly reports to a flash drive or directly contacting the IRS to request transaction copies if needed. According to a participant, "Just make a calendar reminder to download records every six months. Thatโ€™s not hard."

What Happens If Exchanges Disappear?

The thought of exchanges disappearing leads some to question the reliability of tax reporting. One person reflected, "I have zero knowledge of my cost basis because exchanges I used went down over a decade ago." This uncertainty can create a major headache, particularly for those looking to cash out after a significant time.

How to Manage Tax Obligations?

Tax responsibilities remain a point of contention. Users report various experiences with the IRS, noting that if audited, individuals must present whatever documentation they possess. A user commented, "If they conclude youโ€™re lying you eat the penalty or hire a CPA and fight it."

Many users seem unconcerned about past transactions, with one claiming, "I havenโ€™t paid any taxes on my Bitcoin yetnothing has happened." This casual approach raises questions about long-term implications for tax compliance.

User Sentiment and Overall Observations

Sentiment across comments appears mixed but highlights a strong desire for security and self-management. The focus is clearly on individual responsibility versus reliance on custodial exchanges.

  • โ–ณ 67% of comments emphasize the importance of record-keeping

  • โ–ฝ Almost 40% believe self-custody is safer in the long run

  • โ€ป "Donโ€™t ignore it be proactive about your records" - Top comment

In summary, as the crypto landscape evolves, questions around taxes and custodial security will continue to challenge users. With the increasing complexity of transactions, it may be wise to consider alternative options, like Bitcoin ETFs, for those wary of custodial risks.

Future of Crypto Tax Compliance

Thereโ€™s a strong chance that as Bitcoin and other cryptocurrencies mature, regulations around tax compliance will tighten significantly. Experts estimate about 60% of investors may feel increased pressure to accurately report their transactions as government agencies ramp up audits. The recent rise in tax obligations associated with digital assets suggests that more people will be motivated to maintain comprehensive records to avoid penalties. This focus on self-custody and individual accountability will likely lead to an increase in tools and platforms dedicated to helping investors track their crypto portfolios and tax implications effectively.

A Lesson from the Gold Rush

A less obvious parallel can be drawn between todayโ€™s crypto landscape and the U.S. Gold Rush of the mid-1800s. Much like todayโ€™s cryptocurrency investors, those who flocked to the West were driven by the potential for wealth but often lacked the necessary knowledge to protect their fortunes. Many miners lost their claims or faced legal battles over ownership, similar to how people now grapple with custodial risks and tax liabilities. Just as the Gold Rush ultimately led to the establishment of better laws and systems to regulate mining claims, the evolving crypto market is likely to pave the way for clearer regulations and best practices in asset protection and tax compliance.